I just put two long-term rental properties on the market that we rehabbed in desirable area of West End Boise and demand is a little lower than expected.

He's on SSDI (Social Security Disability Income) at just under $1,500 a month and he wants to do some wholesales to make some extra income.Lets say he does a deal or multiple deals and makes any assignment fee on it/them and the profit exceeds 1.5k which is higher than his disability per month.

As for capital, I will be utilizing my HELOC for initial fund on first deal.

Quote from @Miguel Del Mazo: I just set up a new listing on FF today, and I asked myself the same question. 

Mid-term rentals could be a sweet spot between short and long term depending on where you are and what your market looks like.

Typically, HUD charges a daily fee for extensions, which varies depending on the property type and the number of extensions requested.To request an extension, contact your HUD representative or the Asset Manager handling the sale.

Once you have a few deals, like maybe 10 under your belt and they get to know you, they might be more flexible on how much they will lend.   

Unfortunately most have made lifestyle changes relying on checks that will never be cashed but can't fault the inexperienced investors with the amount of materials online, social media etc. where coaches, mentors and gurus share the ease in which they generated massive wealth in these neighborhoods.

Considering the high deductible on House B, I am only filing a claim for House A, and coming out of pocket for the cost of repairing or replacing the roof for House B. 

In that case, you can take out cash through a loan without triggering a taxable event, even if you use that cash as a down payment on another multifamily property.