Now most of them use www.erentpayment.com, much easier for me to track although it takes about 3 days before the money is transferred to my account.

Then he can foreclose upon you and you can also have a forgivable caveat on the mortgage.I have done dozens of JV's/OP's and mortgages are just so much easier as they leave your investor secured, attached to title with everything laid out and clear.

I've bought shorts vacant, tenant occupied and owner occupied.It can be hard in my area too...I wonder if the townhouse has monthly fees that could cut into the cash flow, and to what extent those fees cover maintenance of the exterior...On the plus side, since it's an end unit, maybe it would be easier to rent?

STOP...there are much easier ways to do this.

It is much easier to lose money quickly than to make money quickly and people trying to make money too fast usually end up doing the former.

That might make it easier for you to fully take over the house when you're ready to "buy".

I could atleast fly to Chicago and clean out the unit so that it is presentable to the prospective tenants.

Just have to find one like that - may be easier said than done, but they are out there!

If the bank accepts, we have 48 hours to send them an Agreement of Sale.I'm offering all cash and I would really like to waive all contingencies to make the decision easier for the bank, but the one thing that I'm stuck on is the title.

Financing your primary is much easier and the terms are better.