Hawaii Condo Investment decision

[Ryan O'Leary]

Hello BiggerPockets community! I joined about a month ago after I purchased my first investment while stationed here in Oahu. It's a 3 bed 3 bath condo in Ewa Beach, HI that I'm living in while renting out a room to a young military couple (all utilities included). 

My question is whether or not to hold onto this property after I leave here in May 2021.... I'm tracking on trying to get cash flow every month (after putting money aside for repairs, big projects, etc) with rental properties but I don't think it will be possible with my condo after I leave, especially with the hefty condo association fees and paying a property manager. Should I be okay with paying a mini car payment (approx $100-300/month) once I leave, which would be the leftover expenses from the new incoming tenants' rent, paying a property manager, covering the mortgage, and still covering HOA fees?

These condos have been going up 5-6% every year, so I was wondering if either 

1. hang on to it, pay the $100-300/month when I leave and use the income from my current tenants as a down payment on my next investment wherever I'm stationed next. Possibly sell it in 6 years rather than 3. 

2. Sell once I leave, use the 1031 exchange and buy a bigger 3-5 unit complex at my next location and put 50-75k into renovations, while living in one of the units. (Wouldn't know where I'm going til 2020, but would most likely buy).

I know it's a lot of information, but I'm thinking ahead for the next 3 years. I appreciate any and all feedback from the community. Thanks again!

[Zander Kempf]

@Ryan O'Leary

What did you end up doing? 

Generally I also advise my clients to hold property for the long term. Real estate has a long history of consistent appreciation, so as long as the cash flow is positive and the property can support itself, I would put some local property management in place and rent it for as long as you can.