(It was 8'3" before the city made him widen for safety) I'd love to just buy his place and adjust lot lines, but he's putting it on the market and will ask the moon no doubt. 

You will need to be very careful though as the areas vary, not only by blocks but actually street by street.What your looking to spend and your safety level will dictate more of what areas to look into.   

That being said, a large developer may have to update or put some money toward roads and traffic safety in order to get approvals.

I've had tenants with bad credit but they always prioritized rent amd were wonderful tenants.

Usually you have to serve notice to them to allow them to correct the problem and then if they don’t then file for eviction.You may also want to make sure your front door is set to automatically lock when closed so if the tenant is just careless the door would at least lock on its own for your own safety.

Take that list and prioritize it. 

Here we are two months later and I have started a conversation with them regarding the water bill, liability and property safety due to the pool.  

They have to apply, have a site visit, pass inspection (safety stuff usually) and then get certified for section 8.

Buy with enough margin of safety and you'll be fine in any market... 

Once that vision is in place then you simply prioritize your time accordingly.