Both loan servicing companies and insurance companies can be such a nightmare to work with even under normal circumstances.

-Your current STR seems seasonal, so even without a mortgage, you may not achieve year-round cash flow.

Nor would I pay retail for a property with that low proforma return even though I like PR.  

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

Quote from @Lei Wei: Ko Olina is beautiful.How would you even make that work?

Quote from @Martin Streich: @Sami Gren  it is illegal to edit a contract midterm, even with the tenants consent.

So - somewhere 2 hours away, or somewhere you like to vacation in, or where all your family lives, or where you plan to move someday.Too many people are trying to do exactly what you're doing - pick a market based on a formula - and they end up buying a random 'cheap' property thousands of miles away, turn it over to people they've never met or even spoken to, and then... lose money.  

Normally the escrow agent will want mutual sign off even if its clear the contract terms indicate one party should be awarded the escrow funds.

Even if you rent at a break even or slight loss, if you could have 3 years of rental income offsetting your mortgage while realizing 3-6% appreciation, could be worth it, especially if you think appreciating for this area will exceed national averages.

Hey, even a broken clock is right twice a day, right.