If we were to move forward with the purchase of the second single family I do think we would be able to Brrrr this property into another STR, again if that is not successful we could always sell and make a profit (purchase + rehab should be about 75% of appraised value if goes as planned).

Would it be a wasted effort if I did?

However, it would be cash flow negative if I were able to assume the mortgage or buy it with 20% down at the market price. 

Tulsa has some promising areas for new construction, especially at the price point you're aiming for.You might want to check out East Tulsa and Broken Arrow —both have been seeing growth, and new construction options can still be found under $200K in some developments.

@Tanner Johnson  Surprised a town of 30k would be considered rural.

I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?

Also if anyone has connections for local wholesalers that would be great. 

My name is Arthur  E I have watched my avatar video and also have the Great pleasure of being able to greatly appreciate your kindness. lets do great deals together.

I would start by thinking who do you want to rent to?

A local attorney should be able to advise you on that.