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. 

Use that number and divide by 12, and when your adjusting your specific numbers, ensure to change the tax rate because those sites default the tax rate based on sales price.

I'd strongly urge you to hire a public adjuster. 

If they are taxing you at the 6% for 100 additional square footage, I would try to get that adjusted so you don't overpay.

I think your expenses are too low, and if you adjust properly, its likely to be close to break even for you. 

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!

@JD Martin Those adjustments make total sense to me!

A few years ago I would have said convert it to a rental, but it's not the sure bet it used to be when 25% of our tenants are refusing to pay rent. 

I bet you can.

Or would you say your best bet is to manage the complex (if even) properties yourself?