I've got a decent network in Chicago already, and it would just take time.The end game would be to not work for anybody but myself, and turn, say $800k into retirement money 10 years from nowAJ - the issue with recapturing, is that in order to pull enough equity out of this existing home, I'd need to make X amount working a sound job in the city.

Make sure all final permits are issued, and the approved plans and specifications are referenced in your construction contract.

What other scenarios could I possibly run into besides property value decreasing that could cause issues?

I lived there for 3 weeks and then had to move back to Fredericksburg VA for a multitude of family issues.

Just like a shower, if you have tile and you don't maintain the grout and or caulk as needed, it is not going to last too long and you are going to wind up with more maintenance issues.  

Know that you will get phone calls / texts when something goes wrong or if your tenant is having issues w the property, etc.It all boils down to personal preference, goals, etc.Good luck!

I have a piece of land I've been holding on to for a couple years outside Tampa that would be great for BTR multifamily if only we could address the wetland issues.

Technically, believe you need a real estate brokers license in WI to legally accept compensation for managing a property you don't own.That aside, given the short-term nature of your services, probably be best to do it with a retainer fee and hourly.

The #1 biggest issue is the random but more consistent issues caused by people.Of three fires since buying my first park in 2018 two have been arson.Fortunately, this fire was minor and I probably just need some new carpet and paint.

@Lee BrewerI'm not a seasoned landlord, but I am very seasoned with writing leases and dealing with tenant-landlord issues from my work as an agent.