As mentioned you also can hire a property preservation company to come winterized it as wellAt this point in time it shouldn’t need to be winterized in Chicago but it’s always good to look and think ahead.

Just a heads up - if you have strong relationships with church leadership and are getting into real estate, the YIGBY movement may be a great place for you to work in. 

My wife and I have two reliable vehicles but I decided when they were paid off to start saving right away for the next one by making car payments to myself. 

If I can't find it in a 15 min search at the recorder, then I would go ahead and ask. 

I have gone ahead with painting Navajo White for all the walls, and Ultra White for the trim and plan to use this color scheme throughout all the units eventually.

Welcome to the community, you are already light-years ahead of most people with getting into real estate at your age.

Hello Everyone,I was talking to an investor in regards to financing and his suggestion was to get a 500k loan to put towards all current debt, but wasn't sure all the factors that may be implicated with going this route.My current portfolio has 2 properties (1 LTR, 1 MTR = 370k), and current debts: HELOC at 54k and a vehicle at 40k. 

Honestly, reaching out to property managers is a great idea, and I’ll go ahead with that.The problem is that a good contractor is sometimes an asset in itself that can be hard to share.  

(long response ahead)First off, I just want to say I see you—and you're doing the best you can under some tough circumstances.

You've (likely) got another 60-80 or more years ahead of you.