It depends on what exactly you are referring to with gap funding.

Are you only referring to damages in excess of the deposit?

Any person over 18 should go through the tenant screening if they are living there...they don't necessarily need to be on the lease, but there is another area on the Chicago Association of Realtor's lease to add occupants.

Professional guidance can be obtained from local personal experts experienced in your particular niche.  

This is a good reference for myself and personal private lenders.

From personal experience, this can motivate them to do a final deep clean before handing over the keys.Finally, for peace of mind, you might consider consulting a local real estate attorney.

Are there local hard money lenders that will actually talk to you or is it pretty hard to get a real person on the phone?

I will return to this situation in the end of this post, but first let me show you why the age of a person can be tricky when it comes to the IRS.

@Dan Groveyes, go to meetups (real estate or business) and meet people in person and build a networkbut... no offense... i don't think funding an entry fee in second position is a particularly compelling investment

They become advocates, eager to refer others to join our network.