Since your family member is paying the PITI, there could be questions about whether these payments constitute rental income or gifts.If you're the legal owner, proceeds from the sale would typically go to you.

Probably even a bit of a bubble going on.

I find that when it comes to local advice, Facebook groups are typically the best place to go. 

I would also look at how much are you going to make on this and where are the headwinds of the market moving in this area.

You can look at their nightly rates, occupancy and amenities to see if you can make a go of it.

Most HML lenders cap at 75k-100k minimum (with some going as low as 50k but I personally don't know one that can do 30k).

I can learn a lot more about a firm talking with someone on the phone than I can by going through a website.

For example, if your lease expires 12/31 how many people are actually going to be motivated enough to move after the holiday season and in the midst of winter?

We're willing to go to nearby towns and cities to do deals and start the income flowing. 

This isn't going to go well unless the house you bought is in one of the A-grade suburbs.