I generally have possession of the property terminate at or before noon for the outgoing tenant and begin around 4 or 5pm for the incoming tenant.

They will presumably also maintain a decent cash flow.I would take his new money and either continue to buy new properties or hunt for rehab deals and then once rehabbed and rented out go back to the bank and refinance and repeat that process over and over again.

It spies on your outgoing emails and on your phone calls to save you the data entry hassle. 

So therefore this outgoing tenant currently has the only key to the unit.I have reached out to the tenant twice to inform her that we are getting ready to re-lease her unit before she moves out.

There are different situations and different models for income/outgo, and different markets for cost/rents where an analysis that is as general, and can best be described as using "fudge factors"...then making decisions based on that "fudged analysis", should probably be flushed out from the start. 

I always say “I will email you the application “ but sometimes I just forget to send it out, go figure.

On the tenant side, some of these were in such high demand, you had to lease very early or know the outgoing tenants (I knew a lot of people that leased the same place for 2-3 years of school).

Previous owner was using the “buddy” system for moving in and out.  Going

Wondering if we keep the properties, will it result in more of a loss in the long run with constant outgoings for repairs and empty properties.

If an outgoing tenant leaves a roach problem, we wanna call a pest control service ASAP and charge it to their security deposit.