I don't have a business account or federal tax ID for the business since it has just been me thus far.Can I just 1099 him at the end of the year for what I have paid him?

Nevertheless, I paid zero out of pocket for the whole process due to this legal plan.  

The problem with gap funding is that the HML is in 1st position and they are paid first.

I am curious how other investors here operate in terms of assigning contracts, double closing, assuring they get paid, contract specifications, and so forth.Would love to hear from Indiana investors but all feedback is welcomed regardless of your location! 

Trying to get paid for referring someone else to buy a house from a wholesaler is illegal.4.

Since you did not buy in the hottest hood and were at the top of the market, there was zero appreciation, zero hood improvement, zero buyers prospects improvement, you are lucky to sell it for what you paid and maybe break even for your troubles.Now if you really do your research and you find that needle in a haystack TK that is in the next up and coming hood, the whole story changes perhaps.

If we agreed to say 100K down @ 5% for 30 years and paid 40K in interest per year and 15K of principal.

The shorter loan term is killing your cash flow, BUT you will have the property paid off in 15 years.

Even if you had an FHA loan originally (which it sounds like you don't), you could another FHA loan assuming you could show the old loan was paid off at closing (and there are other legitimate reasons you could have two FHA loans at the same time). 

You do not have a contract with them so they will not get paid by you.If the tenants are paying for a PM, which is extremely strange, you will need to inform the tenants that they may no longer hire a PM or that the PM must conform to your standards.Is this a commercial rental property.