Need advice on feasible real estate strategies to live in 2 cities (Chicago & LA)

[LaRon Phillips]

Greetings BP'ers!

I have a job opportunity that would require me to spend 6-9 months in Chicago and 3-6 months in LA. I’m based here in Chicago and I’m currently renting a 1BR/1BA condo (south loop) and I’m pretty much prepared to buy my first home financially once my lease ends in January.  However with the job opportunity I’m trying how to figure out the best way to manage this while splitting time between 2 cities. Obviously, I don’t want to buy a place that I can’t rent out when I’m away and end up a situation where I’m paying double rent/mortgage during that time. I’m a real estate newbie but here are two of the ideas that I’ve been mulling over. First world problems I know…lol. But any advice/experience is greatly appreciated! Thanks BP’ers!

1) SHORT TERM/FURNISHED RENTALS IN BOTH LOCATIONS

This would be the path of least resistance I suppose but obviously this would pretty much eliminate the opportunity to buy property in Chicago. And buying property in LA? Forget about it! lol.

2) BUYING PROPERTY IN CHICAGO AND SHORT TERM/FURNISHED RENTAL IN LA

This would be my ideal situation. However, the challenge I see here is being able to rent out the Chicago property while I’m away because of the condo association mafias that prevent you from renting out your property on short term basis…and I would assume something like AirBnB would be considered heresy. I guess condos that don’t have a doorman would be easier to pull off since there wouldn’t be anyone obligated to pay attention to who's coming in and out of the building. Otherwise it would depend on who the immediate neighbors are I suppose but you never know who you’ll end up living next to so that’s pretty much a toss up. I’ve heard people talk about avoiding this issue with multi-family units (3 flat, 4 flat, etc) but in the areas that I’ve looked at I haven’t seen many multi-family units that had the “trifecta” of good quality (A/B), good location, and reasonable price point…but then again I’m new at this so I’m probably overlooking the actual potential out there.

I’m doing ok financially: annual income is (and will continue to be) 250K; 100K cash saved. Debt free.

Any recommendations/considerations are greatly appreciated.

(Apologies if I'm posting in the wrong section)

Thanks again!

-LP

P.S. Happy Father’s Day to the dads out there!