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

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. 

So I understand to scale a training business many times you have to outsource ( don't know if this company is doing that) But out source your lead gen funnel.. pretty tough for the actual owners to respond to all the hits they are going to get if they are out on the web with mass advertising.. 

If you plan to Scale. 

Scaling your business to a point where income is not guaranteed to creating a more or less stable system also took many many hours.

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.

And if the house isn't currently selling at the price you've set... that means the appraisal may come in lower too. 1 - Doesn't matter much at this scale of the business.

There is much better scale to learning from people than small advancements on a computer.

Likely going to start with private equity from family/friends but exploring other financing options to quickly scale once I get going.Thank you in advance!

If it goes well and you can stomach it, then scale up.