But either Freddie or Fannie (or maybe both?)

FHA will not use any short term rental data.Something else to think about - any reason why you wouldn't use a Fannie Mae loan here?

If you are going to be an owner-occupant, want a low down payment, and are planning to do a renovation, the FHA 203k and Fannie May Homestyle loans are your best optionsHow do you know the property is currently upside down on the mortgage? 

Then mortgages get collateralized and sold to Fannie or Freddie so they can keep lending and make money from the original fees.

You could also use a Fannie May Home style renovation loan which a conventional loan and require 5% down vs.

I am not able to take equity out of my condo because it is currently on the blacklist due to HOA fixing the roofing and a Fannie Mae rule stating, if more then 50% of the condos in that community are owned by investors, I may not be able to refi.

Non conventional just means the loan will not be sold to Fannie/Freddie so they do not have to follow those rules.

Many banks securitize their loans (bundle them together) and sell the loans to Fannie Mae or Freddie Mac, while continuing to service the loans, that is collect your payment.

., the appraisal for 5+ is at least $2k-$3k) and the financing structure by lenders because Fannie/Freddie don't generally buy loans for commercial properties.So, for you personally, the biggest driver for the type of your next property is probably going to be the amount of a down payment/equity you can put in the property.

Additionally, Fannie Mae and Freddie Mac will sometimes temporarily suspend the income cap on their HomeReady and HomePossible programs, which allow purchases with 3% down.