But, assuming I go thru with a refi, would I be better off at a higher monthly cashflow and extending the loan another 30 years... or would it be best to go with a 15 year to take advantage of a lower rate and paying off the rental earlier?  

I'm thinking worst case scenario, I don't rent it out to anyone, my holding costs go down to around $1200-$1300 if I don't save for any repairs/cap ex and utilties much lower, and then each tenant I put in would just make it much cheaper for me to live for free! 

My rough estimate is 50k-60k for rehab to get it to pro forma level. 

If you really want an attempt at this property just put in an blind offer at what you think it's worth (or even lower so you got some room to negotiate).

I recently found someone who knows of a resort property where he can get it for significantly lower than it is worth,.

As a buyer I love when the appraisal comes in lower than value as it provides me better opportunity to lower negotiated price or to obtain concessions for items found during the home inspection and I employ the best home inspector. 

End buyers have also walked away once they have seen the lower price that the seller is willing to sell for.

End buyers have also walked away once they have seen the lower price that the seller is willing to sell for. 

This lowers their required down payment to 10%.There's always something you can do in an expensive market - look for local experts and learn how they've done it!

@Timothy Mackinny You made an absolute very valid point and I got lower rate than this one who I want to deal with at moment but I didn't feel comfortable dealing with them. however the busy builder has no time for my lower cost projects.