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I think I'm making some progress here...

One question though.. how exactly do you get the scale to match between my image file and Google Earth? Can I input custom scale? If that even makes sense.

For example, the PDF I printed off the site, then converted into a JPG, I cropped, is scaled at 1:25,549. How do I match that with Google Earth? Do you eye ball it?

Yeah, so there is no "scale" you have to worry about.  For maps without any control markings, my procedure goes something like this:
- in the Places tree, add a "image overlay" and use your image for the overlay
- drag the 4 corners of the image around the map manually
- rotate the image if necessary
- repeat until you have something close
- zoom waaaaay in to a corner and find some feature of the map image that you can match to the background and drag the image to match it.  The corners and the exact middle of the image are best for this
- zoom into the opposite corner and see if you can lock it into place
- check the center of the image, and all 4 corners
- lather, rinse, repeat

Its a very iterative process, complicated if the image requires rotation.  You can NOT apply a rotation to a Garmin Custom Map, but you can use Google Earth to figure out what rotation is required and use imagemagick to rotate the image.  You then use that rotated image in the Custom Map.

The short answer is yes, but what you want would be better accomplished by a "vector map" as opposed to a "raster map".  We just did a raster map - we took an image and slapped it onto the map.  A "vector map" would place just the rectangle right where you want it.
You can, however, take that .jpg and edit it in any way you want, and place it into Google Earth.  So if you take the .jpg I first made and cut away all the parts you don't want, then you could load it into Google Earth and georeference it and create the .kmz for your garmin.  You can do that with any image you like - the fact that the image resembled the underlying terrain is mere coincidence.

Yes! Let's have a peek!

Do you know how to view the .kmz I provided in Google Earth?

Definitely. I have the desktop version installed. I can do that much! xD

So, do you think the provided .kmz file is "close enough" for your needs?

I have not seen a reply from you, but I pretended for a moment that you were happy with that, so I went ahead and tiled it.
I'm attaching it here, and you can put it on your garmin in the "/Garmin/CustomMaps" folder.  Then you may have to enable custom maps on the garmin.  See here for help with that:
https://www.garmin.com/us/products/onthetrail/custommaps

Yes! Let's have a peek!

Do you know how to view the .kmz I provided in Google Earth?

Step 3 is to consider the size of the map file and tile the map.  We want to wait to do this until you are happy with the map as it is.  So, can you take a peek in Google Earth and make sure you like it?
Once you are happy, we need to cut the big map file into little tiles that the garmin can use.  I have written a script to do this, but there are many online tools that will do it too...

So, the next step is to use GoogleEarth to georeference the file and create the .kml.
In order to do that, we need to have an idea of where on the earth this location is.  Can you give me a hint?

Ok, I found the location of interest, and did my best to georeference the file.  There does appear to be some minor differences (like the roads are not *exact*), but what I have done should place the most precision around those yellow boxes you are concerned about.

So I'm attaching the map in .kmz format.  You can look in google earth to see if this meets your standards, but DON'T put it in your garmin yet.

EDIT
I made a second attempt at georeferencing, and think this second one (map2.kmz) may be a bit better.

This map looks really very small and should not be difficult to convert into a custom map.  I would like to stress that such a trivial thing as a few rectangles are probably more suited to the more "normal" way where you end up with a .img file for the garmin.
We are going to end up with a .kmz file that GoogleEarth uses, and place it in the "\Grmin\Custom Maps" directory on the unit (or on its memory card, if you have one).

So, step one is to convert it to an image.  For this I will use a free graphics manipulation tool called imagemagick.  I use this to convert and manipulate the images (for example, to convert from UTC to Lat/Lon I run it through a distortion using imagimagick).  For your .pdf, I suspect all we will need to do is convert it to a .jpg.

After playing with a few options, here is the command I used:
convert +antialias -colorspace sRGB -density 200 .\Landscape.pdf map200.jpg

I determined that the provided PDF seems to be an image that is already antialiased, so I turned off antialiasing (I know, that + makes it look like I'm trying to add it).
I played with various DPI settings and found 200 to be "adequate".  Going up to 300 didn't help any - this pdf is not a terribly high quality image.
I'm attaching the resulting file.

Turning PDFs to kmz for my garmin is something I do on a very regular basis.  For some reason I'm insane enough to enjoy it.
If you have a PDF that you would like in your garmin as a custom map, I would be happy to try to convert it for you, or even talk you through the process I use if you would like to learn.

Jeff

See here:
https://support.garmin.com/ms-MY/?faq=anfIu3KDAz8PJNUP22XX6A

- Select Track Manager from Main menu
- Select Saved Track
- Select Copy Reversed
- Enter a name for track
- Select check mark icon (or Done)

Your map looks awesome.
My process of extracting the data from the pdf results in something not quite as blurry as yours...but I get what you are saying about the colors.  I have two maps adjacent to each other with VERY different color for the forested areas...very annoying.
I can use imagemagick (and a fuzz factor) to try to pick out the colors and replace them with specific color - that helps a bit, but with the new topo maps I don't have to worry about that...they are much more consistent with respect to color.

How to I make my image appear inline and not with the thumbnail?

Just want to re-iterate to the original poster - if you let me know an area you are interested in, I'd be happy to make a quick map from a single topo quad for you.

I download and convert USGS topo maps into "Garmin Custom Maps" all the time.  It is something of an arduous process I developed, but it could be simplified a bit if you don't care about shading.
- download the topo map you want: https://viewer.nationalmap.gov/basic/?basemap=b1&category=ustopo&title=US%20Topo%20Download
- OPTIONAL: use a pdf viewer to turn on/off which layers you want
- convert the pdf to an image (I use imagemagick)
- OPTIONAL: reproject the image into KML's "Simple Cylindrical" projection (I use imagemagick, but I suspect there are easier tools if you don't care about each and every pixel)
- OPTIONAL: add shading (this is where spend lots of my time)
- georeference your image in google earth
- cut it up into 1024x1024 chunks to meet Garmin's requirements for custom maps
- copy it to the GPS unit

I use a similar process for the satellite imagery included with the topo map, so I have both a topo and a satellite image.

I'm not sure what Boyd means by "low resolution" - I'm attaching an image of some of what I do as an example - that is a tiny part of Big Bend National park.  The entire topo map for that 7.5 degree quad is about 12.000x13,500 pixels.  You can discern cars and buildings in the satellite image.

I'm also attaching an image from the old (no longer updated, but absolutely beautiful) topo maps...Boyd, were these what you were referring to?  Maybe the "newer" old maps are a different resulution?  This doesn't seem low res...

If you would like to point me to a specific topo map I'd be happy to do a really quick conversion of it into a Garmin Custom Map and you can see how it would look on your device.

Jeff

Yes, I believe you and I have discussed MAPC2MAPC.  I found when I used it, that it munged my images terribly.  If I recall correctly, you stated that it was likely an API call you were making to windows - windows was altering the jpg compression and making my nice sharp topo lines into a blur...
I just found the email exchange we had - March 16, 2017
I would say you were very responsive and helpful to my questions, though.

I would like to add that for most applications, I bet MAPC2MAPC is a terrific solution.  In our email exchange, I referred to my process as having "stupid-high" standards which I may have to abandon.  Well, I'm not smart enough to have abandoned them....yet.

I make a lot of custom maps.  I have found one of the biggest difficulties I have faced is that many maps use different "projections" than google earth or the garmin.  A good example of this is the topo maps and imagery that come from the USGS.  If you look at the map as provided from the USGS, it is mostly a trapezoid with the bottom slightly longer than the top - and more importantly if you look at the lat/long reference marks they are definitely not "square" as Google Earth is.  This is probably done like this so a simple measurement on the paper map is "true".
In order to rectify this I find these reference marks and measure them, and I figure out where the tick marks should be in order to square off the image.  I feed these measurements into free image manipulation software (imagemagick) using its "polynomial distortion" routine to force these tick-marks to be squared off.  The end result is that imagemagick "streches" the image (pixel by pixel) so that everything is shifted into place.
http://www.imagemagick.org/Usage/distorts/#polynomial
That makes georeferencing the topo map (and the image file) trivial.  They now have reference marks for the lat/long, and they are perfectly square as google earth needs.  Additionally, the shadow images I make from DEM files are also squared off (the DEM data is on a squared-off projection), so now the projections on the topo map and the shadow image match - it really makes a difference.
Just out of curiosity - does the map you are trying to georeference have any sort of callibration markings on it?  Is it a map I could download and take a peek at?
Jeff

This is about the best I can find:
The Perry-Castañeda Library has some online maps to download here:
https://legacy.lib.utexas.edu/maps/india.html

It looks like the best they have to offer is 1:250000, the most recent from 1981:
http://legacy.lib.utexas.edu/maps/jog/india/

That link is a text-based list of maps for download, which isn't very intuitive.  But at the top of the list is a link to a clickable map where you can find the area of interest and download actual maps in .jpg or .pdf formats.

You didn't mention what format you need the map in or what device you are using - making custom maps from PDF/JPG files for my Garmin is something I do quite a bit, so if you happen to find a usable map from that list I'd be happy to try to show you how to get it into a format a garmin can read (a "Garmin Cusom Map").

After poking around a bit, I have found these two offer maps for your area of interest:
http://legacy.lib.utexas.edu/maps/ams/india/ni-43-16.jpg
http://legacy.lib.utexas.edu/maps/jog/india/txu-oclc-224039079-ni43-16.jpg

So, IMO, you should not waste any money pursuing a large screen device for Garmin Custom Maps, it will be expensive and very limited.

I am a long time lurker and very infrequent poster who gets a LOT of mileage out of Garmin Custom Maps.  I find them to be very useful and honestly, my enjoyment and usage of my GPS would be very limited without them.  I think the key to understanding their limitations is key to using them effectively, and Boyd has done a pretty good job of citing those limitations.
If your need detailed custom images for small areas (like a farm) on a relatively small handheld device, Custom Maps will fit the bill.  But its important to keep in mind that the capacity of the device can be limited.  This can be circumvented by carrying multiple memory cards, but I have never found that to be necessary.
If I remember correctly, I have put 4 USGS Topo quads on my Oregon with no problem (they were 300 dpi "prints" of the official USTOPO maps) along with 4 600dpi photo images of the area I went camping.  That is some reasonably high resolution (I can easily see individual trees and the 3 foot wide trail in the photo) and covers more than a generous area for something like camping and backpacking - about 30 square miles.
The drawback is that I have to manage the files on the memory card every time I go camping to a different location.  Not a big deal to me - I move some files around on the memory card as part of my prep for the trip.  The bigger drawback, honestly, was converting the projection provided by the USGS to work on the Garmin - but when it comes to math, I'm a glutten for punishment and honestly enjoyed the process.