I had *contractor* come in to look at everything and he said that the wood by the kitchen sink as well as the wood in the front closet had water damage (maybe from wet shoes?)

That is great to see that you are finally looking to kick start your business in REI, I was just in your shoes 10 months ago and I can't say that I had a bad time.

I think in your shoes I'd have put in my original offer and wait for the counter.

If you read this paragraph with a dramatic British accent, you'd be a shoe in.

If I were in your shoes, I would go the route of raising her rent to $850 and taking a chance on her.  

I was once in your shoes.

They were looking for direction on where to start in the real estate process, and I tried my best to give them the information on what I would do in their shoes if they didn't have the funds to pay realtor commissions, closing costs, repairs and everything associated with getting the house sold.

It's not exactly a "fair" assumption but you have to put yourself in the shoes of an owner who's being solicited on a platform where it takes about 3 minutes to create a fake profile and/or pretend to be someone else.  

My point in spelling out the above is that if I were in your shoes, my honest opinion is that I'd do my homework and be as wide-eyed and intentional as one can be in terms of where and what I purchased.Both of the Christian's in this thread made a good point that jives with what I'm getting at.

I was in your shoes in 2009.