This can easily be covered in one paragraph.

I consider the Due on Sale clause a low risk / easily mitigated --- just refinance. 

That we can't evaluate investments in many markets right now in terms of cash flow positivity? 

Are you looking mostly into comps in the same neighborhood when evaluating a deal and seeing if a deal would work?

You can't, easily anyway, say that just because its a 50/50 ownership that only half the monthly payment applies to you or that since the "other owner" took out the loan that they are responsible for it. 

So my question is this is there a service that would help me evaluate a potential home for short term rental. 

I would consult your attorney before using some of the above mentioned methods as here in CA, you could easily get sued for some of those.Asking with your sob story is step 1.

Also, many utility companies have services like energy audits (free) where they come and evaluate the unit and let you know where energy and heat loss is happening.

A project like this is probably 9 months assuming you or your GC can actually line up all the trades properly  even without using hard money and including interest holding costs monthly can easily be 600 yo 800 bucks, over 9 months that’s around 3200 to 4800  See this article on typical holding costs and how to calculate them https://www.flipperforce.com/h...

Rents are currently at 1,000 on each side, but can easily be increased to 1400$-1550$, and the mother in law suite can bring 700$-800$.