Most of the pain came in the beginning when I had to obtain experience doing things I wasn't good at, didn't know very well or didn't want to do.

Pain in butt to work with but well worth it.

My suggestion is eat the pain and try to talk to them and get it done what you need to. 

@Gary Garrett You have a long winded question here but I recognize the pain.

The truth is that finding the right contractor is a painful and expensive process.

He told me about how it was a pain having to do it twice.

But here I am, trying to put a really strong offer in on a home and I’m not sure if I should go in with the mindset that it’s a 3b/2ba 1,895 sq ft or a 4b/2ba 2,055 sq ft… Seeing as I’m going to rent this one day, if I myself decide to get it assessed/permitted as square footage (which I don’t know how much of a pain it truly is), I ran some rent estimators online (RentCast.io) and the rental comp differences between those two scenarios is about $2,275/monthly vs. $2,600/monthly, which is huge!

That's what those under-educated so-called financial expert fools advising HUD gravely FAILED IN THEIR LACK OF INTELLIGENCE TO FIGURE OUT BEFORE CREATING THIS brow-beating, emotionally-destructive, mentally painful, soul despairing REVERSE MORTGAGE INDUSTRY! 

Also, they go over the landlord pain points and show how to alleviate those.Rent Responsibly would be a good resource to start with regulations etc.

@Tom ServerI agree that installing on top would be a huge pain to undercut everything.