House hacking is going to 'save' that rent money, get you started in investing, and teach you more than any book you've read.

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

Joining REI groups and meetups will teach you so much and it’s also where you’ll often find deal funding, partnerships, and the right people for your team: contractors, investor-savvy realtors, attorneys, etc.Even though I didn’t house hack myself, I’m extremely thankful for the networks, lessons, and partnerships I’ve built along the way.

Structuring three to five properties with consistent rehab standards, similar rents, and documented income makes underwriting smoother and often opens the door to portfolio or blanket-style investor financing.

If it were my property I would finish the inside off in a modern, sleek style which would go well with sauna and cold plunge idea. 

If you want to master direct bookings then you can go with Mark Simpson  from the UK who wrote the book on direct bookings.They all specialize and are good at what they know and teach and not so good at teaching the things outside their niches.

Quote from @James Jones: Edwin, sounds like you’re moving in the right direction by starting small and letting each project teach you something before scaling up.

totally love this example. a hard lesson for sure but something that teaches fellow investors a lot that shapes how they do deals in the future.  

Furthermore they teach you outdated methodologies that may have worked 5-10 years ago.

It was real Pawn shop style real estate financing.