I enjoyed what I did building cool bridges and hotels, but I was not too fond of the daily in and our grind.Jumping ship has brought bigger challenges, but I am happier tackling them with people I love working with.With respect to real estate & being a landlord, it's honestly something I do NOT ENJOY that much either (dealing with HOAs, repairs, vacancy, etc.)...unless you can buy properties and completely offload the property management, which was and is hard for me to do with my scarcity mindset. 

You can find great 2-4 unit buildings at reasonable prices (compared to New York City), and many of them need to be fixed up, which is an added bonus of equity if you are willing to tackle a renovation.I'd suggest somewhere along the blue line (train) in the northwest part of the city, where you can find some priceless neighborhood vibes.Plus, the real estate community is unmatchable...tons of people willing to give you a hand up.

I guess land trusts are no use, besides stopping the spam calls.

I agree with people here that Airbnb is not even close to a major problem to tackle in real estate.

You will never find a place with more spam and unscrupulous posters and tricks than in Facebook investing groups.

I think the site you used to start LLC is spamming you for more $$$

Bringing together like-minded operators to collaborate can spark innovative ideas, refine processes, and tackle shared challenges. 

How to compete in a competitive multifamily marketA couple of recommendations for tackling any market with strong demand: - View properties promptly.

You make such a good point about concentrating on paint, trim, doors, etc …I do this all the time with my rentals - I build to a level I’d want if I was living there, not necessarily what the rent could justify in finishes.I’ve got some issues that are far more important to tackle before the luxury fliers I might take.  

I would add it to FB market place and craigslist (though you may get a lot of junk email, spam calls on the latter)