I think I saw you at the Chicago multi-family club on Monday, but didn't get a chance to say hi.I am considering firing back up our Airbnb, which we took off the market for a while...we are in a prime time area (Logan Square) and 5 5-minute walk from the blue line.You make some great points on restrictions making it more favorable for the actual operators and also about the slow and faithful midwest market. 

I’m planning to invest in real estate in Yonkers, NY, and I’m being intentional about setting myself up for success.

Writing back to follow back up on the post, as promised.

Biggest lessons: don’t rush, vet everyone, and have a backup plan for delays. 

So with careful mortgage planinning between your title timeframes (title seasoning as lenders like to call it), planning your income or tax returns, and how long you live at each property while you're house hacking them you could in theory get a HELOC on each primary residence before you leave them and buy the next. 

I'm planning to invest in my first property about a year from now, focusing on the Dallas, TX area.

We recently got denied by the city on a condo we bought where airbnb is ALLOWED but the building was in a planned development area. 

You can maybe give it a week or two and see how it turns out but then have your listing plan ready as a backup. 

One thing that might be worth checking—does your insurance cover any of the secondary damage from the sewer backup or electrical issues?

@James Mc Ree most tenants aren't really serious about Payment Plans and will say anything to try to stay longer!