As a compromise, I am also looking for a single family residence with a detached mother-in-law unit in the back that might help with the mortgage.

From my experience so far and talking to other investors, there are a ton of cash buyers in the chicago market, especially the southside in the particular areas I'm looking to get in.My question to anyone who has experienced being a newbie in a hot market would be how did you overcome it, and find your first deal without compromising your criteria?

The compromise was that instead of wiring them all the money back and reclosing, I would wire the title company the money right now to redeem the ground rent ~$1200.

Is the built in privacy provided by the land trust and LLC asset protection compromised in any way?

You only need to put 3.5% down, so cashwise it won't get in the way of other real estate goals you may have.My first deal was a 4-unit up I bought with FHA 3.5% in Santa Clarita.I lived for free (as opposed to paying rent) + enjoyed cash flow + built equity so it definitely didn't compromise my cash reserves.Good luck!

4) What would you be prepared to compromise on?

Structure of the house cannot be compromised.

However, her mom is going for more chemo, which means her immune system is compromised. 

Gives the impression you're willing to "work with them" on a fair compromise for repairs.But if it boils down to a matter of "he said" vs.

That way, if you receive an approval that has a something other than $0 and $0, then you call the negotiator and try to make them compromise.