I believe this is a much better and faster return on my investment and is a smarter move all the way around because I won’t have to get town approval to rent garage space like I would to turn my duplex into a triplex.

If you're making decisions based off of fear of what others think of you... then you might be better off buying a nice multifamily property and living in one of the units. 

Do you have any recommendations on which cities/ zip codes you find better and which company would you recommend for property management?

Better to buy fewer but higher quality properties.

With both of these strategies, I would look at the rehab as a way to bring up market rents so you can cash flow a bit better, and just sit on the property for a while until you can build up enough equity to cash out or sell. 

This is putting downward pricing pressure on the classes below it, as people move up for a comparably better unit at a relatively reasonable increase in cost. 

I don’t expect free mentorship and believe I could bring value in many ways (paying for time or even better bringing money into a deal where I can learn along side)End goal is transitioning out of SFR and deploying $800k-$1M into a scaleable asset.

Looking to get better and smarter each and every day, putting one foot in front of the other.

General contractor in business for 40+ years with an opportunity to acquire someone else's unfinished rehab for ~$2M with an ARV of $4M - $6M depending on whether we finish the existing project or tear down and start over with a better design. 

I am happy to shoot you a PM with some Chicago insurance referrals...I also know @Jason Bolt here in BP is active in that space.I think the better question besides cost is are you properly protected.