I would wait for the next major downturn if you are wedded to investing here.If you are looking for a passive experience in real estate investing there are other options where you can invest in growing markets all over the country.

Thanks @Lucas Carl, that's a wedding photo from last month :-)  "The ol' gray mare ain't what he used to be".

They actually got married on the property & had their wedding pics taken there.

We have been living together for 7 years so the wedding can happen whenever we want, but don’t want to have to pay $100,000 in taxes because if it.

January 30 - Weds - at 6PM.

I've seen too many bat crazies  and what are you going to do when the tenant says your handyman stole their diamond necklace off the nightstand or someone takes a rock and cracks open the lockbox and breaks into their house and the tenant holds you liable.

If you have time an excellent event is the every Wed at 10am-12 full timers meeting. 

In an average year I get less than 5 inquiries from them, and it's usually someone coming here for a wedding or graduation that just wants to stay a weekend. 

My understanding (I'm not a CPA) is that if you plan business related tasks on Monday and Tuesday and plan on spending Wednesday, Thursday, and Friday at the beach, you can't claim the hotel expenses for Wed-Fri.

There is a DuPage Co group that meets up every 3rd Wed of the month in Downers Grove at Emmett's Ale House starting at 6:30.https://www.meetup.com/DuPage-County-Real-Estate-I...They also have a Facebook grouphttps://www.facebook.com/groups/898079283660130/I'm not sure if there's any closer to where you're talking about, though.