@Jordab Ohana Can you narrow down the type of commercial leasing that interests you? 

By the time you take out a trad. cash-out refi, you'll be eating a bunch of fees, which will chew into your theoretical 5% arbitrage spread. 

The lifestyle question is one that you must determine, then narrow down what parts of Chicago provide you with that lifestyle, then we can really answer the question- How is the market doing in those specific neighborhoods?

I haven't 100% narrowed down my market yet, but once I do, I'll aim to connect with investors first, seek advice and recommendations and go about building my team this way. 

This is appealing as I want to spread my cash reserve as much as possible. 20 percent down each time will really limit my progress.  

There're also many narrow scope planning opportunities that are less common than those I listed.

When investors see that you’re looking out for them, that you treat them like partners rather than just capital sources, they start spreading the word.

It spreads their risk.In regard to market, there's a couple of different approaches my clients take:1.)

I have many questions and I've narrowed my desired locations down to Hornell, Corning, Bath, Horseheads, Elmira and or Binghamton.

He had a client who was debating between buying a small apartment building in L.A. or spreading out capital on multiple units in Phoenix.. after running the numbers with a dedicated local realtro who actually drove around neighborhoods, he opted for Phoenix because he could get more doors for the same cost.