Looking for Advice Please

[Jerry Rice]

Im looking for advice. My goal is to own 3 properties (New York, LA, Honolulu) . Ive figured in the nice areas houses go for about 800-900k each. I want to own these places, rent out the extra bedrooms and stay in the masters as I travel. Researching zillow ive found places "they say" will appreciate in value. Heres my financial situation

I own one home with about 400k in equity that i can rent out for 3500-4000 a month

I own a triplex worth 900k that makes about 1500 month net now

Cash I have about 2M

income now is about 100k year

Im in my mid 30s

Should I buy 1? Buy all 3? All cash for 1? Loans on 1,2,3? Id like to keep the house I have now and rent the entire house out

[Kinohi Larey]

Aloha Jerry! Lots of good advice from others here. Wanted to give you another option for your Hawaii property:

Ever thought about purchasing a higher end unit in Waikiki in order to Short Term Rent it?  For instance, you can spend between 700-900k on an Ilikai unit, rent it out short term for 200-300 a night depending on the season, making a gross income of around 5-7k a month (75% occupancy rate). Then whenever you plan to visit the island, you can block those dates off of your calendar and treat it like your home. 

Might be easier and more appealing than having to share a place with your renter when you’re here. Also make some cash flow  while you’re not here, as well as appreciation. 

Just a thought.  Hope the best for you! 

Btw, you would happen to be a hall of famer wide receiver would you?? Haha

-Kinohi Larey