Assuming you received a title policy, I suggest you immediately file a claim with the insurer and not the title agent which issued the policy. 

I am assuming you already filed your 2020 taxes anyways, so unless you amend your return, it is probably too late.

They will handle the process of title work, settling taxes and filing mortgage paperwork.

Going along those lines, I hope you always mailed everything to the HOA via confirmation signature required or emails were saved in your sent file and everyone cc'd. 

do I submit them the latest mortgage statement as part of the filing? 

Do you think I should bring a note pad or would that be wierd/awkward?

In Illinois IDFPR will go after an unlicensed wholesaler if someone files a complaint.

We are new investors and want to maximize our tax bill and also file for an LLC to move at least the Reno home into.Thanks for any input!

Tell him rather simply to just go away, otherwise the PFA will have to be enforced, and that will lead you to filing an eviction against him.

If that LLC is a disregarded entity meaning she is the only member and it does not file it's own tax return, then again the activities of the property are also shown on her personal tax return.