The goal is to continue growing the management business with our portfolio.

I've been investing in one market for 10+ years and my vendor list continues to evolve and never had the mindset of assembling a team I can rely upon.

If you do decide to help them out and rent continues to be late simply have a talk wiht them and remind them that rent helps pay your bills and since you did them a solid ask for the same in return.  

I’m here to connect with like-minded individuals, exchange ideas, and continue learning from this incredible community.

Whereas I (and others) continually urge them to stop being lazy and do their own research....go on VRBO and ABNB and look at the competition. 1) What are they charging?

This year, let's prioritize learning and adaptability, recognizing that continuous growth is key to staying ahead in an ever-evolving world.Networking and collaboration will be crucial as we navigate the changing landscapes of industries.

From my own personal experience and from others I think most reach the "tipping point" from self managing to using a PM somewhere between 5-15  units, especially if you have a W2 and want to continue to scale. 

Still learning about how it works but this is my understanding today.We have decided to continue with this deal, due to the location of the property, the fact by licencing the extension and renovating the building we should be able to get a price increase from a buyer as a private home.

I'd expect prices to continue to appreciate, so the longer you delay, the more expensive things may be. 

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.