Making the leap into STR vs Buy & Hold

[Michael McCarthy]

So I am extremely interested in STR investing. I have a close friend that is successful at investing in a couple STR as passive income on the side and I am highly interested in doing the same. I have seen some of his numbers and how well his number are now and pre-COVID, and truly believe in the model. I want to make the same leap into STR, first as an investment on the side, and maybe one day, have the ability to make it a full time gig.

I have a couple people that I could possibly partner with on this who have had a lot of experience in real estate, but not in the vacation rental market, especially STR with AirBnB and VRBO. I want to present the model to them where they would solely be capital partners and I would be the managing partner, but need some extra advice on the benefits of STR over long term buy and hold.

Areas I am extremely interested in are Sevierville/Gatlinburg region, but also know the Gulf Shores/Destin region very well too (I was stationed there before during flight school). I know they have been extremely popular in the past and have high occupancy rates most of the year, and especially in the future post-covid, will continue to be very popular. I may get some push back in wanting to invest closer to where I am stationed (coastal carolina region) with areas such as the OBX, but I am not as big of a fan of the dependency on a more seasonal region.
 
Apologies for the long post but what does the group have to say about this? Thanks!