I can be paid $3,000 a day for my technical skills yet I am not worth anywhere near that doing administrative tasks.

It something we've considered, the review process from the county is quite extensive and back in 2006 they were almost anti-development, things might have changed a little since then.

A quick Google search should give you a rough idea of market rate for most common remodel tasks.

He doesn't like talking to people, but does like repetitive tasks he can do while listening to music..could be a great chance to get him involved in the business

I'm guessing owners fall in a couple buckets:- Don't automate and can't handle the repetitive tasks of more than a few rentals (probably not most of the pros here)- Buy several STRs, achieve financial freedom, and are content to stabilize the properties and cashflow- Focus on new revenue streams outside of STRIs there any reason not to scale STRs like LTRs?

Look at the top 5-10 task you really need and see what system does it smoothly. 

In any business of course, its key to choose the most bang-for-buck task or work so if creating a website is going to swing the needle the most, then by all means!  

Trading a pool of mortgages is not small task nor is it a quick time frame.

However, if you average a good hourly wage and can arbitrage that time into more income producing activities, it makes total sense to sub out property management since its a lower cost per hour task than what you can be doing.

I don't think Hawaii has as big a storm problem, but I recently found a condo that has a $580/month in Maui have big extra assessments for the construction of anti-erosion measures like storm walls.