REAL ESTATE NEWBIE: SPLITTING TIME BETWEEN CHICAGO & LA...ANY ADVICE?

[LaRon Phillips]

Greetings BP'ers! Over the last few years I've done some "career hacking" to find a better work/life balance for myself. Well I've achieved that goal after 7 years! I've gotten things to where I can work from anywhere as long as I have an internet connection. I've always wanted to split-time between my 2 favorite cities: Chicago in the spring/summer and LA during the winter months of course! Since the job situation no longer requires me to be rooted in any particular place I started to think that maybe I can make my dream scenario of a bi-coastal lifestyle a reality (I know that Chicago isn't technically "coastal" but you get the point! lol). I'm currently renting here in Chicago and I have another year on my lease but next spring I plan to purchase my first property. I'm a total newbie to real estate so this would be my jumping off point. So over the next year I want to take the time and formulate a decent REI plan and make this happen in a way that allows for solid growth financially. So naturally, I'm turning to the Bigger Pockets collective brain for ideas, strategies, life hacks, etc that would make the most sense as I put the pieces together. I'm trying to figure out where the blind spots are in terms of logistical challenges that may arise going forward. Any advice/constructive criticism is all greatly appreciated. Thanks!!

GOAL/IDEA

• Buy my first property here in Chicago.
• While in LA I would find a short term rental there and rent out my place in Chicago using airbnb or short-term corporate rental, etc and find a property management company. The mortgage in Chicago would be covered by my renters which would essentially allow me to avoid paying for 2 places at once when I’m in LA. I’m thinking that renting in LA would be more cost effective due to the super high cost of property there…but this is coming from my limited knowledge of the market there.

QUESTIONS

• Does it make more sense to buy in Chicago and rent in LA or buy in both places?
• What type of property is best to buy in this situation (e.g. condo, townhouse, 1BR, 2BR, etc)?
• What areas of Chicago would it make the most sense to consider for property purchase?
• What are some of the logistical/financial blindspots that you all see or that I should anticipate?
• Have any of my fellow BP’ers had any experience in pulling off something like this?
• Is this plan realistic? lol

Thanks everyone…wish me luck!

-LP