But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Get a small MF you can house hack and start that way.I'm not an expert on the auction scene, but, from what I have read, that is a challenging first step into investing. 

Qualified applicants that get priced out of rapidly improving neighborhoods will move into these areas but it seems like they aren’t biting.High quality, lower income applicants aren’t stupid and they won’t settle.If you think this area is a losing proposition, I would think about selling and not banking on hope.In regard to vacancy, I don’t consider any area that has average occupancy (economic and physical) below 95%You might pay more for a better area but time will treat you right and you’ll make a ton of money in equity over the long term.

Do you currently work with an expert CPA who is helping you maximize tax breaks with your real estate investments?

I think we all get fatigued from time to time, and I think it's worse when things are "slow" because of economics or demographics or whatever.

I've helped 6-7 different investors move money from Oregon to Wyoming in the last 15 years and they are all happy they made the move.Consider finding a market that has a better long-term outlook, economically and legally.

What makes you an expert that the unit is in a great location & condition and the market is hot, relative to the property manager?

Work with a tax expert and real estate attorney to finalize the deal and navigate zoning or financing complexities.This post does not create a CPA-Client relationship.

The city of Cairo and Alexander County as a whole are in a very depressed economic situation.

I'm no expert, but do know for a fact that you are much more likely to find "good deals" off MLS – through mailing, cold calling, off market groups/connections, etc.