Anyone have experience with 30+ day STR/Medium Term in Honolulu?

[Corey Cawthron]

I’m in year 8 of investing with a few different strategies and experiences under my belt. I recently acquired a single family home in Charleston, SC that I’m renting furnished for 30+ day (ideally 3-4 month stays) and it’s going very well. I also own three long term rental multi family properties in various locations. 

I am starting to think about acquiring a condo in Honolulu to also rent for the STR/MTR (definitely 30+ days to avoid STR requirements) but my biggest question comes in the form of Leaseholds. I've done some light research on buying into a Leasehold property, and while most things in real estate don't really scare me, this is the greatest unknown to me at this point. Does anyone have any recommendations or past experiences they can share with acquiring leasehold properties? I've seen some that are good through 2046, 2050 even, and I feel like that's a long enough period for me to be comfortable with acquiring it, because really it's more of a chance for my family to use it from time to time, even if I break even and don't make much cash flow, I'd be happy. Thoughts, comments, and concerns are most appreciated!