Here is a presentation I made describing the benefit of doing such vs a regular investment.

There are still tons of MLS deals getting done regularly. 

I fire clients regularly. 

Be sure to check out the free tools BP provides to help analyze deals you may have and also market insights.

How do other regular condos perform versus them? 

Might be an additional cost there.If units are updated, capex items look good, leases and tenants look solid, and there are no other regular expenses besides the 5200 in insurance/property taxes then I like this deal.  

Of course "hoping" rates will come down is not a sound strategy so finding a way to assume a loan that already took advantage of low rates is a great option.If you were starting over and targeted a large SFH, would you try to maintain the property in a way that would still attract regular homebuyers (not investors) if you needed to sell?

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

You can check out this group to know who the players are.

I'm in Ohio and we see those lower loan amounts pretty regularly.