.- It's not profitable for them to search for under-market priced houses, figure out repairs needed or what other problem is pushing the price down and do even more for a newbie investor that has analysis-paralysis and may never buy anything.Some questions you'll want to share the answers to with any agent you choose:1) Are you paying cash or getting a mortgage?

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

You want an investment that pays for itself, including mortgage, taxes, insurance, maintenance, and even some money set aside for a reserve to cover vacancies and capital expenditures.

And, it's amazing how many closing costs are junk fees that we as investors need to pushback on paying for ourselves and our clients.

Now if I pass that income as management fees to S-corp, I pay $3.5K (SE tax) + $800 (LLC fee) + $1700 (CPA + bookkeeping) = $6K in total.

I like the fact that one and a half units pays all bills.

My parents had to stop paying the mortgage and I could feel the stress radiating through the home every time I visited.

Just sell and pay off that loan or two.

So either you pay for the repair out of the idle cash in your account, file an insurance claim and use those funds, or rollover/transfer funds from another retirement account to cover the cost. 

This is the first time I have done something like this, where it was for other reasons besides not paying rent.