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Routable means, that map supports routing. A suitable GPS can trace a path between 2 points, which uses roads from the map. When map is not routable, GPS will use straight lines instead (well, probably great circle path).

Address search is a separate functionality, where GPS can convert street address into geographic location.

While maps created by Garmin usually include both features, this is not necessary the case for free maps, where creators often lack mapping data or programs to create fully functional map.

BaseCamp is a convenient tool to manage maps. You can easy transfer maps from BaseCamp to GPS but there is no perfect way to do opposite - transfer maps from GPS to PC. People usually want to use maps on both devices, so  IMHO better to offer maps for BaseCamp than a file for GPS.

Well, it's not all automatic, but I offer the same download for Windows and Mac.

I assume that you are using Window 7 or newer. I hope that you have already installed 7-zip. If not, please download it and install, its site is here:
http://www.7-zip.org/

Using Windows Explorer, find downloaded map archive on your HDD and right-click on it. You should see pop-up menu, which include some commands added by 7-zip. Use 7-Zip -> Extract files. This will open a window with some options. Please select destination directory (folder) on your HDD, you can use button "[...]" next to field "Extract to". You can create new directory if necessary. Then click "OK" and archive should be unpacked to selected directory.

Next navigate with Windows Explorer to previously selected directory and enter a subdirectory with a name like the map. You should find there files named like "install_US_South_Atlantic_OSM_Topo.bat" or install_US_South_Central_OSM_Topo.bat, depending on a map. Extension ".bat" could be invisible, it depends on settings of Windows Explorer. Files should have description like "batch file" (I'm not sure, how it is presented in English version). Double click at this file to execute it and map should be installed for BaseCamp.

I hope you know BaseCamp, it is a free program from Garmin. BaseCamp can be downloaded from here:
http://www.garmin.com/en-US/shop/downloads/basecamp

With BaseCamp you can browse map, design routes, collect POI etc. And you can install maps to your GPS. see this guide:
https://www.gpsfiledepot.com/tutorials/how-to-load-maps-on-my-garmin-gps-unit/

Yes, maps are routable and search for address should work.

Map can be routable but still without search index. Which one have you installed?

Are you currently in Europe? Please make sure, that your current location as shown by GPS is inside area of the map, that you are testing. If necessary you can fake position - switch GPS into demo mode (system menu - GPS), move map view to map area, find a POI or mark a point there, click it, select form point menu "Go" and then "Move to location". This is a procedure form Dakota, I hope Oregon works similarly.

When on map area, try to search for address.

However, long term I'm trying to decide if qGIS can meet my needs since it is free open source and looks pretty good. Pretty sure it can easily re-project too.

QGIS is a very useful program but a bit buggy. It can reproject maps.

Other tools for this task are command line tools like GDAL. It is bundled with QGIS distribution, so the easiest way to get this working is to install QGIS.
http://www.gdal.org/gdalwarp.html
http://www.gdal.org/ogr2ogr.html

Reprojection is only relevant to Raster data as Vector data has no associated projection.

All Garmin maps are WGS84, but vector data in general do have projection, which should be converted to WGS84 for creating maps for Garmin.

Now in the past, I think Garmin's software would apply elevations from wherever your track/route crossed an elevation contour on a regular topo map. Not sure if that system is still supported on their newer software and devices.

It still works in BaseCamp.

The number of objects for GPSMapEdit is limited by available memory, which is about 2GB for 32-bit executable. I think it is still more than could be contained in a single img tile.

Does your layers contain specific object types? Like for example one layer with parcels and second layer with buildings, where you want buildings to be drawn over parcels?

In this case, loading shp layers into GPSMapEdit merges all data into single layer. You have no direct control, which objects are drawn on top. To make your map look correct in GPS, you should design a TYP file, which contains graphics properties of objects including draw order for different area types.

What do you expect by these actions?

There is no layers in Garmin's map, the closest thing would be levels, which are kind of predefined resolution or simplification of a map. You can insert, delete or edit level's properties in menu File -> Map Properties -> Levels.

NOAA charts are free to download:
http://www.charts.noaa.gov/ENCs/ENCs.shtml

I'm thinking about converting then to Garmin maps. IMHO license allows for converting and redistribution, but I'm not sure if I could waive all liability, even with disclaimer, that they aren't intended as primary means of navigation. Any advice?

I am having issues downloading OSM too routable for the northeast into Basecamp. I am using Basecamp 4.6.3 & Mac OS 10.12.5.

Could it be USA Northeast OSM Topo Routable? In this case downloaded file is an archive compressed by 7-zip. You need to unpack it first. Try to use keka for unpacking:
http://www.kekaosx.com/en/

I tried to load 2.76mb of data on a 2gb and it told me I couldn't as there wasn't enough room for the maps.

That kind of message usually suggested some error in maps installed on PC.

Do you mean this map: https://www.gpsfiledepot.com/maps/view/239/ ?
This map isn't compatible with 60CSx, so your problem is connected with some other map in GPS, but I can't guess which.

You can try to change all labels to upper case in the real map from your 60CSx with GMapTool:
http://www.gmaptool.eu/en/content/label-style

Actually this won't work for the map from the link above, since it is a raster map, where all labels are a part of a jpg picture.

And I suggest to try my map of Hawaii:
http://www.gmaptool.eu/en/content/usa-hawaii-osm-topo-routable

I created an .mp file which has shown routes on GPSMapedit, then I convert it into .img file using the same program

GPSMapEdit is an editor only, it doesn't compile maps. It is able to invoke cGPSmapper for compilation but if you are using cGPSmapper Free, then it doesn't support routing. Maybe try mkgmap.

My goal was to not have to depend on cell signals needed for my smart phone GPS

You move in opposite direction then I. I prefer to drop Garmin and use a phone

Garmin City Navigator maps are based mostly on data provided by Here (previously called Navetq). You can get the same maps on your phone for off-line navigation, it comes directly form Here. Program is called Here WeGo and is available for Android, iPhone and Windwos. While not so sophisticated navigation like a nuvi, it should be comparable to City Navigator on Montana. Did I say it is free?

On Android I tend to use OsmAnd, which is a navigation program using OpenStreetMap data. Navigation is a bit crude but I like it and I like OSM idea.