--reach out and thank them upon getting the booking and ask if they have any questions--send a "Welcome" email or automated message during the week prior to arrival--reach out the day after arrival to ask how everything was the first night and ask if there is anything that the property needs--reach out at the end of the stay (that morning or within 24 hours) and ask how everything was, anything to improve, anything to add to the house and then offer an incentive for returning guests.My 2 cents,Mike Absolutely stay in your place as Mike said.You will see things the cleaners will never let you know about.We stayed in our PF will putting up the Christmas decorations and found a cracked plastic shelf in the fridge. 

But the diversification may be through a number locations of the same type property, as expertise in one area trumps diversifying into areas where you lack a competitive advantage.  

It's free to sign up for an account and the savings account has a very competitive interest rate.

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

You can offer whatever you think is appropriate and message the seller with your reasoning.

4) How do the finishes & amenities of your property compare to competitive properties?

You purchased in 2020 so you're experienced in high-demand, competitive markets.

Starting to look at possibly investing there.Great, but also expensive and competitive.

@Deirdre Lizio see a lot of competiting PMCs start with a pledge of doing it better than "what's out there".Always interesting to revisit them 3-5 years later - after they've experienced the reality of challenging tenants AND owners.Look no further than Evernest: they started out with flat fee management at $99/month and promises of better & fairer service & pricing.Now they're at 10%, capped at $199/month - wonder what changed?

The seller setting the amount is illogical, and anti competitive because they set the amount under the threat of a group boycott if they offer too little.