Team building in this case is just a distraction, but nothing wrong either with preparing some names ahead of time.

These situations are extremely hard financially, emotionally, mentally, and spiritually. 

We are wondering if he should go ahead and sign up for a real estate course.

So, we are trying to figure out quickly if we should go ahead and have me put it on the MLS price it high enough to pay off the original mortgage and the other liens on the property (we don't know an exact number on this, but we think it might be around 30k) and see what happens.

I would go have the seller call them just ahead of closing and soon enough to avoid the cheques going out in the mail and then have you pick them up on the first of the month in person.

Something I have noticed is we tend to occasionally have a tenant who seems to think that rent is due on the first for the prior month.Despite late fees, constant reminders, etc. they will without fail pay their rent one month late.Aside from threats to evict, is there a better way to screen tenants like this out ahead of time?

That is light years ahead of anything we have here in Illinois. 

I will go ahead and ask my attorney ;)

Appfolio is light years ahead, having used both.

So if you're going to do it, either do it sooner rather than later OR go ahead and get that mortgage before you do so.