I'd like the building to be within 10 minutes walking distance from a Brown Line L stop, ideally in Lake View, North Center, or Ravenswood.

Unless you have some sort of subject matter expertise or access to an unfair advantage (cheap labor, ways to source off market deals, etc.), index funds are likely to provide an equal or better return with a MUCH lower hassle factor and more liquidity.

I started with Ken McElroy's books, because 1) clearly he knows what he is talking about given his track record and trajectory and 2) because I had easy access to them. 

It's set up to be accessible and appealing to your audience.

A potential challenge with a HELOCs is they are based on the current appraised value of your home, not the improved value, so you would need to make sure you have enough accessible equity.

Now I'm not gonna be Mr Tour-guide for any/all who want to stop out and just look around but if you go through the steps and are serious, we have built out acquisition strategy HECK-YEAH I'm gonna say come-on-out and we'd carve out some time to do market tours together AND I'd equip you to do some self study/exploration. 

Hard money is expensive.Some questions to ask yourself to assess risk:Do you have access to a reliable contractor who can complete the work on time and stick within a budget?

How is access in the winter?

If you’ve got strong tenant demand, proximity to top employers, or even access to public transit, you’re laying a solid foundation.

Early testing of this new system indicates that it’s a pain to get access to.