That in and of itself isn't fishy, per se, but what was fishy was the person picking up didn't sound like a property manager to me. 

Beckett thanks a ton, I'll reach out to pick your brain a bit.

Most of us have made mistakes - try and pick our brains and avoid making the same ones.  

If you haven't already read it, I'd recommend you pick up the book 30 Day Stay by Zeona McIntyre and Sarah D.

A lot hinges on that. 

Also, you should have her security deposit, so you could also use that to pay for the new lease, and tell the new landlord that you are paying it out of her security deposit.I would start by asking some probing questions to your tenant, such as, I'm considering paying for your 1st month to move out by xx date, do you have a new location picked out?

I've seen newbie owners step over dollars to pick up pennies.

Once you pick your market, get down and dirty and learn as much as you can about it.

Then blot it, don't rub it to pick up the oil. 

Before your meetup gets "tax-creative" - no, you cannot take turns picking up checks for the group.