Buying vs Renting on Oahu

[Paul K.]

Hey BP family! I'm in the process of moving to Oahu and would appreciate some advice. I'm military and will be moving there for a minimum 1 year assignment, likely will extend to 4+ years.

I currently househack a SFH in Dallas. All my housing expenses are covered and will cash flow even more once I rent my room out when I leave.

The condo I am looking at purchasing is a 2/2 in a great location, one dedicated parking spot & plenty of guest parking. I like the option of the 2/2 in case I do get a roommate later on, friends/family visiting, etc. I would prefer to not have a roommate in Hawaii, but would be able to rent out the extra room for around $1500-1800.

The numbers:

$630k VA, 0% down, 7% interest.

Closing costs: $10k

Principal and Interest: $4200

Taxes & Insurance: $200

HOA: $700 (this will increase in a few years when the building undergoes pipe replacement, unknown how much but I'm estimating around $300).

Electric & Internet: ~$200

Total: $5300, likely $5600+ in a few years 

If/when I move out, I would likely be able to rent the unit for $3300-3500 or $3600-3700 if I rent by the room. Ideally I would refinance in a few years.

Potential rentals (2/1 or 2/2) I’m looking at would cost me around $3300. Likely would not have a roommate if renting.

I could cover the $5300 but it is def not ideal going from $0 in housing expenses to $5300 and would probably get a roommate in this case. 

Other considerations:
I wouldn't be able to use remaining VA entitlement anywhere else with 0% down (except other very high cost of living areas).

Extension not guaranteed but I’m in the guard so I have a lot more flexibility/freedom than active duty in where I want to live/work.

More affordable condos ($520-550k range) are an option (typically no/limited guest parking, fewer amenities, etc). This would reduce monthly payments to around $4700.

Is there anything I’m missing or other things/strategies I should be considering?

Thanks in advance!