Are there any mentee programs or anyone looking to mentor that you could refer?  

This is what people casually refer to when talking about tax free cash flow.But your mileage will likely vary.

Yes I invest in midterm/short term rentals myself in SA and I help many investors in my network and on bigger pockets find rentals here in San Antonio/New Braunfels.you can read some of my references and testimonials on my profile or google page 

If you do, do you refer to this as a pet deposit, or as an additional deposit?

Knowing the good and bad would be much appreciated.Hey Jonathan, are you referring to East Cleveland as in the city?

This will allow you give a reference point on how much potential rent you can receive.

So, real estate agents may do it part-time, but rarely do they do it well.Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

I'm also asking for contractor, CPA, insurance, and legal references from the property managers and will speak with / cross-reference them before going forward with one. 

By "on and off" I was referring to taking a break from looking all together this past summer.

That's NOT a viable plan (for reference, see years 2007-2011).If you can't hold it profitably, sell it fast and move on!