Second thoughts and opinions.

[Brandonlee Kuhaulua]

Aloha Everyone, working on acquiring my first deal!

I apologize for such a lengthy post. Wife and I had recently changed our lives around by paying off all our debt of $90k, and fixing our credit scores. We still have a substantial amount of capital on the side to invest into real estate. I've been educating a lot lately on REI. Our initial plan was to purchase a multi-unit home on Maui to house hack. However, the market here is supper expensive. We have reached out to about six lenders with pre-approval numbers that we are happy about but understand that its not enough to buy a home and only enough to buy a condo which is not in our criteria.

My pivot here is to start investing in STR's and acquire a passive income to afford these multi-unit LTR's on Maui and in other states across the U.S.

You might be thinking "Why not just buy the condo on Maui and do STR from it?" I have analyzed countless properties here on the island and the math is just not mathing. Purchase price is very high, and HOA fees are out of this world.

Ive done my research on STR's and picked three locations where the numbers make sense and are affordable based on the capital we have. These three locations are; Kauai, HI | Florida (Destin, Kissimmee and Orlando) | Pittsburgh, Pennsylvania I have networked with experienced investors in the STR field and are being very helpful with providing a gameplan into STR. For right now I was directed to choose one location which would be Kauai, HI

I guess what Im asking for is opinions from others that also have experience in STR's (Airbnb) if I'm on the right track here. Thank you and looking forward to connecting with you.

[Ryan Moyer]

I have 25 in Kissimmee and also have some experience and Destin.

Straight away, Destin is an appreciation/lifestyle market. If cash flow is your goal, it's not the right place. If lifestyle or appreciation are your goal it can be great.

Kissimmee you really have to have at LEAST $100k+ to invest into theming to compete. With that, it can be okay. But it's still not going to be the top market for cash flow. Can be decent cash flow alongside other advantages such as lifestyle (if you like visiting Disney), more stable year round income (not relegated to one high season where a maintenance issue could knock out a huge chunk of your annual revenue), and very little regulation risk (if you buy in the approved STR resorts) and little long term demand risk (people will always visit Disney).

For pure cashflow, probably none of the ones you picked are the ideal spot. Cash flow means random tertiary markets no one has ever heard of where the competition is low. If you're looking for more than just cash flow you have to weigh those other points like entry price, regulation risk, appreciation, etc.

Feel free to pick my brain on Kissimmee, I'm happy to share anything I know even here publicly.