The properties just end up going to the politicians friends for pennies on the dollar.

Driving by dollars How did you finance this deal?

Considering the figures of 95% occupancy and $750/night, it's akin to a software business having 2+ customers on a $21,500/month subscription EACH.Unlike software startups, real estate offers "easy" bank loans, so each dollar invested effectively becomes $2-4.

I realllllly don’t want to sell because I don’t think it has had enough time to appreciate, but I also don’t want to waste thousands of dollars every year in the likely event that my co-op board will not allow me to keep renting out my place.

The primary on the house is asking for a dollar amount that is not too far off from the property's ARV.

i can't / don't want to do 25% down payments anymore.i'm also dollar cost averaging into the stock market. 

Imagine making millions of dollars throughout your career and then having to pay Uncle Sam 30-50% every year instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of the best ways to end up with a much larger net worth at the end of your career.

We have reached out to every buyer/seller agent as well as previous owners to try and get statements proving it was an apartment.The issue is... now we need plans drawn up, a permit issued, and a city inspection on something that was converted decades ago and will cost thousands of dollars and time. 

Typically a worthwhile real estate broker will save you time through efficiency and add at least equivalent value in actual dollars through effectiveness.  

You may need to spend a few hundred dollars to get a lender name change if the new lender requires that, but depending on when you rate locked you may still end up saving money with a new lower rate.