As far as I know the gift limit is around 15k and there is no way he can rationally drive the sale price down due to “needed repairs”.

I had a feeling most would say to hold on to it, just needed to rationalize it again. 

It's just hard for me to predict the future and I like to keep my options open, so I haven't done it.That might not even be a rational way of looking at it - it's probably not - but summarizes where I got to when I considered it a few years back.Also, in terms of multifamilies, I think it makes a big difference if you're paying the utilities or your tenants are.

Everything else is fluff and/or rationalizations.

My rationalization is that I can just evict her if things don't work out.

So not the best answer but hope my story or rational is helpful.

What you are trying to do is rationalize what you want to do inside of your offer, but sellers don't care.

At that point it's no longer a rational analysis of true expected returns and probabilities, but little more than a delusional hope game that often ends up in big disappointment in the longer term.

Don't worry about the ones you missed or you'll start rationalizing bad deals into good ones, just because you are focusing on not missing something. 

Hate to break it to everyone, if you are betting on the majority of people picking the smart, rational, financially savvy route you are going to lose.