(I mean after all they they can go to Airbnb any time in the next 10 years and get a history of first listing date and dates rented.).

I'm not one to bet on it yet.

However if she insists on being on the deed, I wonder if giving her 7-8 thousand like a wholesaler and flipping it would be my best bet, or even giving her a 50/50 or 60/40 share of the (possible) 60K flip. 

The feds  cannot afford to increase rates anytime soon because the economy will surely crash.4.

And I bet when you see the P&Ls/Tax returns on this guys amazing business, it becomes less amazing.Don't waste your time, you're running a business here.....right?

I’m betting now she bought the property herself. 

So, a say $40k net income MIGHT let you borrow $150k (assuming you have no other debts/loans which I'm guessing might be possible if you have $30k saved up).So, the co-signer route is your best bet, just remember it may not be theirs since you will be tying up their credit.Hope this makes sense. 

I know people do long distance STR, but A) I bet there are lots of restrictions against those in Hawaii condos, and B) long distance would not be my preferred way to start doing STR....not by a long shot.If you can't qualify, find out why you can't qualify. 

Please, feel free to reach out anytime if you have other questions or just want to chat!

REI is all about taking risks, and since you only have enough capital to try out one strategy right now (perfectly normal for someone starting out - no, you're not behind the curve) then I would start with your safest bet that is going to make you more profitable in the long run, either with knowledge or cash flow... ideally both!