What is occupancy and rate and how does that compare to your competition? 

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I am curious though, in hindsight, how does an investment in STR in Hawaii in 2012 would compare with other markets over this period of time despite all the regulation headwinds?

The training as compared to other "guru" programs is not much.

It's tough to give a definitive answer without knowing your specific investment goals (cash flow, appreciation, etc.) and preferred strategies (BRRRR, wholesaling, etc.).However, since I'm a Cleveland native and active in the real estate market here, I can offer some insights on why Cleveland could be a good fit:Affordability: Compared to many other major metros, Cleveland offers a relatively low barrier to entry.

The city offers more affordability compared to the DMV area, with many renovated homes selling below 350k giving you a better chance at finding a property that fits your budget while avoiding sky-high prices.

Are there any unique considerations or red flags you look for compared to the traditional rental process?

Comparing workload, a multi-unit property will still require showings, maintenance etc for multiple units.

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Many landlords think of it as the HIGHEST end of rent prices for comparable rentals.