I remember chatting with a good friend of mine, Jared, who once picked up a quirky three-story in Somerville to rent short-term.

Research local market rates to set competitive rents, and consider offering utilities or furnishings to attract tenants.

When you have a VERIFIABLE record of success within specific property types - and typically specific geographical areas, you MAY be able to attract enough passive investment to begin syndicating smaller type deals.  

It sounds like inventory is pretty fixed in the Maui short term rental market, but I'm not sure if that's a safe working assumption for the long term.

Long story short, I am in a bad financial condition as of recently.

Such units are painfully in short supply and sky high demand.

So for the conservative busy professional that just wants to buy a clean house that is the attraction to turn key..

The Left must resist the urge to “help” with short-sighted, counter-productive policies like rent control.

@Rick Soto,Both options have their pros, but here’s a way to think about it given your plan to move in 5 years:Option 1 (10% DP, 2-1 Buydown): This gives you lower payments for the first two years and saves you cash flow short-term.

If they’re facing a short-term financial hiccup and you feel they’re otherwise a reliable tenant, you might consider setting up a plan for them to catch up on what they owe.