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

With 60 doors, not sure how many Titles you have, but that could become a pain to transfer via probate, AND don't forget that probate is public.Well, hope this helps. 

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! 

Time is Money and Tenants are a Pain.

Maybe a higher PP pushes them past the pain of paining Uncle Sam.

i own few condo's in NJ and find the association a pain.

Getting their numbers was a pain...

I would also like to learn about some other pain points you have been experiencing to help improve the product we are building. 

It was a pain to get good quotes and available people to build out spec homes and I needed a reliable/credible GC to qualify for the loans I considered anyway.2.

Find out their pain points, provide immense value to them and expect nothing in return.