Although I believe I can see the path to my first rental easily, I'm having a hard time figuring out how I'd get to the next one. 

There are so many lost opportunities relying on assumptions that aren't accurate and easily verified.

We self-managed 20 properties while working 2 full time corporate jobs pretty easily.  

You should be able to do that fairly easily.

Once you’ve got the hang of that you can easily repeat the process or go bigger.

If it’s a smaller home that has a high occupancy already it may not be worth it, small homes (1-2 beds) that are priced and marketed well in the Denver metro can easily stay over 80% year round.

I also think you could easily find what you're looking for in the Gold Coast - which is a little less hectic than River North and gives you that Lincoln Park vibe as well. 

In a place like SE Michigan, we are lucky in that prices are low enough that you can find deals in solid neighborhoods that easily return well.

Because later, you can easily use it as your mailing list!

You can’t find a seat if you do t come 30 minutes early.