Unfortunately, most landlords don't have the skills necessary to manage their units well.

Congrats on taking the leap into REI and setting ambitious goals—it’s never too late to get started!

@Hamp Lee III I have a friend in Cali who’s looking to get into sober living homes as well.

It's also harder as a small owner to find good services of handyman/cleaners than it is to do the other stuff once it is set up.  

California’s going to have their hand out as well.

It can also be a huge set back when a bad investment is made.

Kristen,I'll add a note that you are allowed to depreciate the condo that you have as well as I didn't see mention on your post. 

I'm sure he did really well with the property - enough so that he could complain about the cost, yet pay it and stay in business- but, I wouldn't buy one unless you had serious reserves, just in case. 

Sometimes this creates appraisal problems.I'm also looking in to VA construction loan as well, potentially for a BRRRR property.

I live in River North and preferably would like to work in downtown Chicago and surrounding neighborhoods but open to the suburbs as well.