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?

It's just like buying a used vehicle...

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.

If they don’t plan to share resources then you’re only ahead on the design and drawing if you partner with them.  

I will provide the counter-argument to the prevailing consensus here...opening up the property to a wider audience of prospective tenants will more than likely get your property rented faster...if your property sits unrented for an incremental two weeks (and you forego one-half month of rent as a result), did you really come out ahead by not offering to pay one-half of the monthly rent to a realtor that would have brought a qualified tenant to the table?

Should I flip her unit after mine or go ahead and get a re-appraisal and refinance to move to the next property, or option 3 (unknown)?