It can certainly be done, but I'd recommend having a solid contractor on your team and holding a fair amount in reserves. 

This group have given me some really solid advice already so I want to ask this.

On the other side of the spectrum you have the investors posting in these forums about the contractor who walk off the job and shares how they hired them to do a SFR gut reno with updating mechanicals, new roof etc. for $45k and is wondering why they are running into issues.  45k is a solid budget for a nice cosmetic rehab on a 1200sqft home.

We have a really solid Chicago community! 

For example, if you're looking for scalability and strong cash flow, multi family investing in areas with a solid price to rent ratio could be a great option.

I don't think it's wise to try this until you have proven experience and a solid partnership agreement.It's OK to scale slowly.

From my experience, cities like Greenville, Columbia, Augusta, Huntsville, Chattanooga, and Jacksonville offer strong house-hacking opportunities with growing job markets, solid rental demand, and affordable multi-family options.

Quote from @Carter Trombley: Quote from @Jonathan Greene: Just earn solid money.

Your plan seems solid so far, good luck! 

It sounds like you have a solid, strategic approach, especially with a focus on value-add properties in appreciating markets.