Given the very low interest rates, and the ability to buy at historically low prices in solid suburban areas with very steady rent demand from A-grade tenants, I think you've misframed this in your mind in thinking that the suburban homes with debt are going to create more stress for your life.

That being said, if pets were in the equation, I would go with a commercial grade flooring.  

I'm a second grade teacher and I've spent the summer researching REI and figuring out my path in this game.

Arti Turfs should cost around $2-2.50 for mid grade.

To level off that kind of dirt to bring it close to street level would require very expensive grading and likely a retaining wall.

I could definitely do some of the work and contract out anything that is above my pay grade.

If you think you're going to find some real estate type selling such information that cares about your success as much as your 8th grade math teacher did, you're mistaken, I'm sure.

A bank may want to see a lot survey or a copy of the recored plat showing the property lines and any easements if they exist.Judging by your question of "if it is buildable" makes me think the developer just laid and road down and didn't do much grading to get the building sites ready.

Even within Seminole co the "school grades" are varied but Seminole is consistently considered by most to be the best overall for greater Orlando. 

What exactly is grading?