And also If you could plan a trip to coordinate with some of the meetups that would be your best bet. 

The time limit to invest is much better than 1031 (in some cased year and a half) and so on. 

I don't think $20k is that far off if you are hiring a General Contractor to manage the project.If you manage it yourself, I bet you could get it done for somewhere between $10 to 15k.  

As important as it might be to know what a GOOD deal looks like, I would bet dollars to doughnuts that it is just as important to know what a BAD deal looks like. 

As important as it might be to know what a GOOD deal looks like, I would bet dollars to doughnuts that it is just as important to know what a BAD deal looks like. 

From my limited understanding HELOCs are typically whatever the current mortgage interest rates are plus 1 point. 6.125% doesn't seem too out of line.

Once booked, you can bet they'll be combing over the photos with a fine toothed comb and a gleam in their eye, and sharing the listing with friends and family (or fellow guests) as they envision their actual stay there. 

I do not know how to limit future leverage, since I have limited cash.

There is a limit on how much mortgage you can pay if its all in your name. 

@John Groseu, a lot of NY-metro markets are cooling due to last year's tax bill limiting SALT and over building, in the city especially.