They do not provide such services, and have every incentive for you to NOT look into such a plan which will deprive them of the commissions they receive for selling you stocks and mutual funds. 

My accountant told me to switch from a single to multi member llc for beneficial tax purposes.I was planning on adding my wife.

I think it could be beneficial to show her the numbers.

It would be beneficial to know if any big corporations or businesses coming to Chicago??

You would then later assign the beneficial interest to your LLC.

My current HSA allows me to invest in mutual funds.

I can see how it may be mutually beneficial.

But, again, folks invest in the stock market all the time, in ETFs and mutual funds, so it's certainly not a bad idea - I'd just emphasize that consideration if you're concerned about not being able to actually see or vet the projects you invest in.

What I'm trying to say is that even though it is typically beneficial to focus on one thing and give it your all, I believe you could do a little bit of everything which will reduce risk, and give you more options.

From my minimal understanding  an LLC is best for buy and holds but for flipping/wholesaling I have heard an S-Corp could be beneficial.