Ultimately, all else being equal, I think you're smart to wait until the end of summer.

The cons of this are that many residential neighborhoods don't allow for rentals, so if we tried these areas and decided it wasn't for us, we would then sell as a traditional home as opposed to a renting it as long term rental or vacation home.I also realize I could rent for a period of time and evaluate but again, then I'm paying someone else's mortgage that could ultimately working towards my own.

My ultimate goal is to flip homes, and many have recommended attaining a real estate license first.

Ultimately, it depends on your credit score/history and your investment situation.

It was a little frustrating, but ultimately I found tenants to take over the property the day after the tenancy ends.  

My Goals: Ultimately, I want to Fix and Flip.  

All the clients that have been with FASS have ultimately went to REDS, Holton-Wise, or Keller Williams Greater Cleveland West.

To be able to take care of myself and give back to the ones that helped me is my ultimate goal.

This starting guide on wholesaling would help a lot https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/

Check out the podcasts and the Ultimate Beginners Guide.