Short-term rental loophole and REPS status are the main paths to follow! 

But there could be reasons like type and terms of financing that make this an attractive option3.

Help me figure out if this scenario I thought up has potential to work or not.First Leg:Purchase Price: $500kDown Payment: $100kClosing Costs: $20kLet's say I want to purchase a short term rental at the price point of $500k.

Most work this way BTW Rates: 9% to 13% (Most Deals are 11-12%)Terms: up to 36 Months (Most Deals are 6-12 months)Fees: 2-4 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 (For loans less than $250,000 $2,500 minimum fee)Max Loan: 65%-70% of After Repair Value(ARV)100% Rehab Financing Available (Require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 2 Weeks)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.

It does not answer every question (are they under/overcharging, do they have egregious cancellation terms, do they have silly rights to sell your property, do they have two and half pages of ticky tack fees, etc.), but something has to go reasonably right for a PM to have 95% occupancy or greater on a several hundred unit portfolio, in my view.

My girlfriend and I are considering investing in a short term rental in St John or St Thomas USVI.

Then the goal would be to either sell it off or keep it as a rental for a long-term hold.

But, I am considering buying a home 300+ miles from me that I can use as a vacation home for myself a few weeks a year and do short term rentals the rest of the year.Question: Can I get a second home/"vacation home" mortgage (10% down) when I don't have an existing first-home mortgage? 

We looked into what was required from the owners standpoint and it turned out he needed a slightly different insurance to cover the property's use for short term rental purposes, even though he wasn't the one actually renting it out.

I am considering starting with Staten Island and Long Island, as they seem to have relatively lower barriers to entry in terms of pricing.