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.

If they need a cash infusion, they'll just borrow against the home. 

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

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! 

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!

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. 

And if the tenant is enough of a pain it will ruin the more lucrative main tenant because they will leave.