@Chris Kay to learn to properly DIY manage you have two basic options:1) Trial & fire on your own, hopefully not making a major mistake that costs you tens of thousands of dollars.- Once your time is more impotant to you then the cost of a PMC, you can hire one.2) Hire a PMC to guide you on your first rental and learn from their expertise.- You can buy additional properties and DIY manage those, perhaps leaning on the PMC for any issues you're not sure how to handle on your own.Good luck:)

Milwaukee is the third most competitive market for tenants in the US.

These are two different things.

I currently use the two family cars we have to conduct these activities, and I am looking to buy a new vehicle that is more suitable (a truck) for the tasks that I have been doing. 

Quote from @Jim Bryant: Two things.1.

So I may be okay breaking even the first year or two. 

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

That may be the path for a year or two while you figure this out.

We own and manage two and one is particularly difficult during the shoulder (slow) seasons.

Couple, unmarried, two cats, 50k in savings, mid 30s, credit over 780!