On whether or not you will qualify, you might just talk to a lender and lay everything on the table before getting a hard inquiry on your credit, then you will decide if you want to move forward. 

@Jason DiClemente I think that's a pretty reasonable time table.

You bringing any skills/outlets to the table with you?

KDP Septic based in Phillipsburg is excellent, they put in a complicated 50K system for us in East Amwell Township in the dead of winter this year (high water table on property so needed pump up leech field system, ground was frozen, they have all the heavy equipment needed for something like this).

Especially if it hasn't yet hit the water table.

If you have nothing to bring to the table you will find it difficult

The whole purchase agreement process happened so fast I’m still thinking about what I left on the negotiation table!

How you going to make any money w/ 30k IF that left on the table.

I brought up the idea of purchasing subject to his existing mortgage from the realtor who is representing him, but they asked how would we report that at the closing table.

Given my current scenario with this recently purchased house, if you were going to rent out to the two friends to offset the cost of the mortgage - would you keep things simple and do this "under the table" without all of the legal paperwork, or would you do this "officially" with all the necessary paperwork and legal forms making me the official "landlord" renting out to two tenants.The way I see it is this.. keeping things under the table would make things simple with my two friends and obviously require less paperwork.