New Investor Seeking Advice

[Darci Aita]

I purchased my condo 7 years ago and it has nearly tripled in value. While I'm excited about this, I really like the location and layout of my place - it's in a nice, quiet neighborhood close enough to the city but far enough so families are comfortable (Oak Park, IL) I'm right by the metra and 'L' (subway) which is fantastic for my commute to work. 

I'm graduating from my masters program without any student loans and I don't have any debt aside from my current mortgage, which I owe about $25k on. 

Should I sell and use the profits to invest in a new place? My concern is the market seems to be a sellers market now, and I'd hate to invest and end up underwater. I was thinking of buying a 1-2 bdrm in Wrigleyville and renting it out with AirBnB. With 81 Cubs games/year, I could bring in at least $225 a night. It's a pretty big tourist location. I'm concerned about regulations though, and wouldn't want to be stuck with a high mortgage and no ability to rent or airbnb my unit. 

I could also invest my profits and rent until I find a great real estate deal - but that means spending $600 more a month on rent (My mortgage is crazy low). 

Here's the breakdown: 

Home sold for $50k, worth $130k

Rent nearby is around $1300/Month (The HOA Prevents me from renting my unit out unfortunately)

Options: 

1-Stay, save up and continue to have a low mortgage 

2-Sell, buy a new place and invest my earnings in non-real estate investments

3-Sell, buy a place in Wrigleyville and airbnb it out while renting elsewhere 

4-Stay, get a home equity loan and do #3 (minus the sell part)

What do you think? Am I missing any options, and what's the best option?