I don't believe our system is set up to send reminders prior to it being due - rent is due on the 1st, which is pretty common so most people have no issues w/ remembering.

A contract would have legally obligated him to perform.

Who is the appropriate professional that I would need to consult about legal aspects and benefits of moving my rentals into LLC?

Beware they tend to give BPO's which are closer to ARV's vs As-is values (as do majority of sellers) so don't leave much room for profit after taking into account holding costs, legal, taxes, etc.  

And for you to know what issues you are willing to take on.

The best way to be certain of market rents is to work with an experienced local property manager and have them go through your property and give you the market rents and what/if anything you could do to improve the property and rents.Short of that, look at similar rentals to yours that are listed and use a comparative market analysis method to determine market rents.Really recommend working with a local property manager for making your ownership experience as passive as possible, for compliance issues related to renting, and to help you scale to more properties leveraging the property manager's time and experience.To Your Success!

So you can DIY and realistically chances are quite low that you'd have any issues, but if the IRS reviews it the fines and penalties will significantly outweigh saving some money by not having it done professionally plus you're either gonna leave a lot on the table or overstate which is a surefire way to get audited.

I would list any major issues in the Summary and tell the buyer to read the entire report for minor issues, like GFIs, sticky windows, etc.

Title issues, seller issues, non-refundable deposits, no inspection period, lending issues, appraisal issues, liens, IRS liens, city liens, no wills, unpaid back taxes, solar liens, and all kinds of other crazy stuff.   

The only issue now is what Raymond mentions above...most lenders require reserves of 3-6mo for approval on their investment loans.