Roofer is neighbors son, genuinely nice guy, want to trust him.

TRUST BUT VERIFY.

Maybe, maybe not.If you do get an option to purchase, be sure to record a memorandum of option (or some such 'cloud' document for your state) so that nothing can be done with the title of the property without addressing you and your option. 

Here's my opinion:I'd start with getting a deal structure on paper:1) Agree upfront how much value you assign to his land, and agree that your shared LLC/trust (or whatever you set up) will owe him that amount when you ultimately sell.

The key for you is Develop trust early on and he may overlook your past inequities . 

Address: 717 W Kaley St Orlando, FL 32805•-I looked into the crime rate, which seems pretty high online, so I am most likely going to shy away from Orlando, but practice doesn’t hurt •-I looked on craigslist and Zesimate and it looks like rent will go for about 1200-1500 for a 3bed, so I’m going to estimate 1200 to be conservative •-This property is also listed for 70,000 – I want to estimate 20,000 for rehab costs ( I am still reading up more on estimating rehab costs) ,but for numbers sake, I will use this number for now.

If you can't get that for some reason, you got to get references and previous addresses. 

I wrote down all the addresses and did the following for the building we desire the most: -Researched and called Cook County Assessors-Researched and called the Water Dept.

I wrote down all the addresses and did the following for the building we desire the most: -Researched and called Cook County Assessors-Researched and called the Water Dept.

Obviously, you should consult with your CPA and lawyer (trust me, pay the fee, it's worth it).