Still very small but being in SF and working in tech I am able to manage everything remotely with very few headaches and be cash flow positive.

I got a call from my HVAC tech today stating none of the work had been performed.

I'm not a boiler tech so this is just speculation. 

If you look back at how almost every area has gentrified in the past, they all start the same way with 'artists' migrating from an overpriced neighborhood into a new low-income neighborhood, and opening up coffee shops & other millennial-esque stores.It sounds nice in theory and I'm a big fan of tech, but currently RE tech is 2-3 decades behind the curve.

I may be going back into the tech sector soon and will need the day-to-day stuff covered. 

I also called a local tech college and they say the idea is good but insurance is the issue.

I also collect in cash from two of my older tenants who are not so tech savvy and I don’t take personal check, so either money order or cash.

My background is in the tech industry.My question: Is the Tampa area a good place to start investing?

Being young, you're probably tech savvy and can figure out social media marketing for a mentor.

Yardi is my main software, but if you're tech-savvy and a real quick learner, you can make almost any software/system to work with what you need.