My goal would be to flip since my part of Arizona is growing at a larger pace than we can have properties available for sale, making it very much a sellers market.I plan on sending out letters on a smaller scale but at a regular cadence.

Makes the regular rentals harder to come by in the right areas. 

Otherwise my regular tradesmen are fine.

Trouble is you cannot rent it out on a regular basis.

Should I pay for a pool guy to regularly maintain it?

I have a career I travel for regularly.

If on the other hand, you don't like your current job and want to use real estate as a way to decrease your regular job, then a) try finding another job you like, b) buy some properties to either flip or rent. 

Sometimes there is a predatory nature here on BP, be careful. 

While I do invest on a regular basis, I get investor loans (more costly) and have to put 25% down for small multis.Best of luck.

I always fall back to the literal meaning of the words and not the implied intent because what seems like a gray area to a regular person will be black-and-white to a lawyer.