A condo that hasn't been upgraded since it was built in 1979 but is identical in every other way to one that has just been rehabbed with quartz counters, shaker cabinets, new black stainless appliances, imported tile floors, recessed lighting, fancy backsplashes, etc will show a much different $/sq ft. 

Is it worth it to get some sort of wifi installed so I can check in on/control the heat?

David Hodge the price per sheet is separate/different.As an example, the roofing subcontractor I use gives me a flat price per square for ripping off an old roof, and installing a new one.

Once the kitchen is installed in the basement, we will live in there and rent out the upper 3 bed 2 bath. 

We have recently installed VCT in two of our apartment units, covering old hardwood that was in bad shape.  

I had one person who moved in and wanted a ramp installed after the fact to minimize the bump from the road to the driveway. 

When their kidneys started to fail they peed in convenient places.Life got immensely easier when we removed the carpet and replaced it with tile.

According to the layout, without actually seeing the roof line, I would assume that the north and south walls of the home are load bearing and if you are going to install a door on the north side you would need to build a header over the door.

After getting a few estimates I discovered the issue was related improper installation from when it was installed 2 years ago.

You don't want to get stuck with installing an elevator or meeting an expensive lighting, or efficiency requirement.