Next step down would be your local banks portfolio products which are usually modelled after Fannie/Freddie, but are willing to make some concessions if you are strong enough. 

I did leave my W2 job to pursue real estate full-time; however, I transitioned to being a 1099 contractor and pursuing ventures that I truly enjoy doing, so maybe a hybrid model?

You're in good shape with the equity you've got, but this might be the point where a lot of people look back and wish they followed the simple buy low and sell high model. 

The IRS describes 6 different methodologies: detailed engineering from actual cost records, detailed engineering using cost estimation, survey or letter, residual estimation, sampling or modeling and rule of thumb.

If so, what is your model?

@Ozzy Sirimsi - I'm in the midst of reading "Millionaire Real Estate Agent" and have been considering looking at Keller Williams because I like the systems and models that Gary Keller proposes.  

Having said that, I'm trying to approach this using @David Greene's model of finding 2BR units with 1000+ sq ft in an effort to buy low, convert into a 3BR, then ultimately cash out refinance.

If you are going to micromanage it (and there is nothing wrong with that, if it's your business model), then having a property manager do the work first is a waste of time, resources and money. 

I live on the north side of Chicago with my wife and son.I've been diving into strategies around innovative short-term rental investing (airbnb, VRBO) and trying to investigate whether a lease-ro-STR model can work in Chicago. 

I'm also very open minded on re modeling a house for a flip .