I do plan to ask her in my follow up but I wanted to post here and get any thoughts before I got deep into the conversation with her. 

Notably, I’m not a big fan of creating deep vertical structures (i.e. where one LLC owns a subsidiary LLC that owns a sub-subsidiary LLC, etc.) unless you have a very good reason to do so.Disclaimer: While I’m an attorney licensed to practice in PA, I’m not your attorney.

Overall, I think jumping into a 6 unit property as your very first investment would be like jumping into the deep end of the pool before learning how to swim on the shallow end.

Anyone know some really good IL Asset Protection Lawyers and CPAs that live and breathe Real Estate?

. ;) It's very true and deep that we are all temporarily able-bodied.

But some of the younger generation given the choice of an iPhone and Social Media VERSUS oxygen to breathe might chose to give up on the oxygen first!  

A 30 year loan will give you more breathing room and you still have the option of paying it off in 15 years.

I would look at Set for Life by @Scott Trench as a starting point, then do a deep dive into house hacking here on the site. 

From my experience: when I purchase in bulk I always want a deep discount, however if I’m buying one item I understand that the margins are not high enough for a deep discount.

They will average each other out but will be very different when you drill down to the details.My advice, is use the big thumb rules for initial quick glance but when you are ready to put in an offer, dive deep to the actual property numbers and do not use the industry averages if you don't really have to.