@Matt Geerts, I can't point to statistics to prove it statistically, but if I only had to rely on one referral method it would be lawyers.

You can check out rental sites to see what is being advertised, but I definitely wouldn't rely solely on Zillow's guestimate.  

I relied mostly on comparable recently sold houses and rents from Zillow.

I've never agreed to allow this, but I fear he may just rely on it and there's not much I can do.2.

Read the rental regs in your area. it's fine to ask or get advice but relying on yourself rather the friends is a better long term plan even friends can mislead you.

Part of the reason for this is it is expensive to have a couple architects on site for a few hours just to take measurements, and part of it has to do with us being able to rely on the expertise of the other trades.

If they are, I would not rely on the current assessment or taxes.  

I completely understand, and this relies on the landlord's responsibility too.

I wonder how Monroe county will allow homes to rebuilt since every lot relies on the Point (ROGO) system.

That being said I have a couple more options.Option #1: Do a cash out refinance on the property with $100k (property #1) and I would be left with the $60k needed for purchase but nothing for rehab and I don't have enough cash to handle this so I'd have to rely on 0% interest credit cards, some cash, and maybe some other type of line or credit or loan with a higher interest rate.