I would not fund this loan knowing that he intends to make it his primary unless you plan to adhere to the associated regulations. 

I thought I was getting an amazing deal but what I'm ending up with is; essentially locked into closing on house where everyone expected the current tenant to leave cooperatively however, he is now planning to stay indefinitely without paying rent until getting evicted.

A sales rep from that company was saying not to worry about it they won't enforce it and they have seen claims paid out... all well and good but what is in writing is what matters when the lawsuit gets filed.

Upstairs currently is a mid-term rental but plan to do long-term after they move out EOY

Do you know your neighbours who may tell you if things aren't going well? 

On the other side, I am planning 15-20 doublewides.

I am in the middle of negotiating a deal with a seller who owns a Sec8 Rental property near Pittsburgh, PA (New Kensington 15068).The tenant has been there for a few years and kept the house well-maintained.The rent is $9006 BD 2 BA 1,555 SQFTCOMPS: ARV - $135,000 | AS-IS $90,000I'm looking to get a better understanding of what Sec8 investors would pay for such property, trying to lock in the best deal possible for these investors.Also, what are the most important things I should look for in these deals?

Indio is currently STR friendly as well as the HOA but I've heard there may be caps coming soon by the HOA - we wouldn't have to worry yet. 

You typically get better terms with purchase money vs cashout refi as well.

Cost Segregation is a commonly used strategic tax planning tool that allows companies and individuals who have constructed, purchased, expanded or remodeled any kind of real estate to increase cash flow by accelerating depreciation deductions which can defer state and federal income taxes and increase cash flow.When a property is purchased, not only does it include a building structure, but it also includes all its interior and exterior components.