You need time to get your feet wet - and doing it on a small scale is WAY safer than getting into a 6 figure renovation.Flips are for one time cash, and rentals are for long term cash-flow.  

No goal, no white boarding, none of that houdini grade D salami.

If you want to scale up and buy more faster putting less down is the best plan.

To increase my capital for investing I have already scaled our 401K contributions back to 6% to take advantage of the company match and aren’t doing any more than that.

A class you will go full scale.

Full time happens with 100+ units and often you see people scale a business on the side, like PM, construction or something unrelated like a resort in Costa Rica ;-) I am no different - I "retired" from my corporate career in 2015 and quickly realized that I can only watch so much daytime TV. 

Got it @Brett Nissen What type areas are these properties in on and A-F scale?

I'm new to larger-scale private capital raising (did a little bit with first airbnb project) and am looking for advice.

If you plan to Scale. 

It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.I'd actually highly suggest Michigan because there is WAY LESS restrictions.