(elderly owners limited viewings)  From speaking with the listing agent, the only 'known' issue is 'bow' in the living room where a grand piano has been sitting for many years and the home is dirty.AC unit replaced 2000, unknown age of roof.Finally to my question, I've read J Scotts book, but I'm not 100% comfortable with the estimating part.  

The sellers' Broker said that the seller was looking to liquidate this property to acquire more property, this was one of his long-term holds and it had always been a good investment for him (basically buy this house, its a great house).After a little back and forth, we get some disclosures from the seller, we learn that the tenant is in arrears for approximately $3 grand.

They weren't going to be able to get to it for 2 weeks and it was going to cost me 3 Grand!

I only owe 8 grand on it.

(wow I look just like this when I am on mine..)....and something SUPER obvious strikes you.. you jump off your throne..you run to the computer.. standing there bend over, as you can not sit down for obvious reasons...and you apply your SEO grand idea...and the next morning...

Or do we go with the "safer" choice of house 2 which we like a lot (but dont love) and only needs a few grand in reno work?

. :-) Never offer more information than asked...the average banker will not be impressed with your grand goals.

It seems as though you don't have as much cash involved on that one & are garnering a grand return monthly. 

This flipper has now listed it for sale for over 200 grand.

If you like, you can throw another couple grand at the situation and sue her but throwing a couple grand for a very low chance of collecting $10k one day is a bad bet.