This is your nature you are not likely going to change the core of who you are. 

If you're looking to leverage the value of your home the best method I know is a HELOC (Home Equity Line of Credit).

There are several tax methods available that can increase your cash-flow on properties you invest in.

Can anyone guide me where or whom to talk to in terms of buying and creative financing or experiences in dealing with a complex of this nature?

I would just refund the days they were unable to occupy, unless the nature of maintenance was elective and not required.

Some of my key takeaways were that it is important to define exactly what you're looking for (Crystal Clear Criteria - CCC) and that, using the stack method, financial freedom through small multifamily investing is tangible and achievable for everyday folks like you and I!

I work in the "what if" industry, so naturally the "what if" in a friends fight comes up.Everything else checks out on both (strong credit, no evictions, no criminal, etc.).

However I may just send the wholesaler this end buyer in hopes they will provide me a finder's fee.If not, no big deal and I move on knowing this is their method and we won't work out.

That method is cumbersome, time-consuming and bogggles my mind.

This perfectly highlights one of the top 3 FILURE methods of thinking; the "oh no, I better be careful to have to to owe/pay too much in tax's" lie.