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Once you have the establishment of the 2 year owner occupancy that's help you to cover the capital gains portion.

I spoke directly with Drew Sygit - the founder of LogicalPM and we spent a good portion of 60-90 minutes chatting about the current portfolio, the issues I've faced, and how his company plans to solve it. 

Did yall agree on the lump sum portion ?

Separate the property management portion out.  

The Housing Authority will discontinue a tenants assistance if they find that they are breaching the Housing Authorities lease also (while we use our own lease for all tenants, the Housing Authority also has their lease with the tenant for the assistance portion), which does make it easier to file for eviction in the event they do not pay their own rent after the assistance has ended. 

Would I have to pay portion of recapture tax in this case? 

3rd federal savings and loan might do it they are based in OH however I think they want to be first loan holder so it would need to be paid paid off free and clear also I was told they have a heloc that they will pay a portion or all of the closeing cost I used them on my prime residence vary good rates however the rep I worked with was very vary slow with responding and pushing things along good luck I will be doing this same thing on 2 rentals soon so be sure and post what you figured out thanks

If there's a part of the job that does not require a license and will not be inspected by the city (such as finishes) I as the project manager have the option whether or not I will give that portion of the job to the GC or farm it out. 

Quote from @Tabitha Jones: Hey Joel, for reporting your hard money loan on taxes, you can file using just the interest portion from your 1099nec.