One is a 3 bedroom 2 bath built in 1953 and the other is a 4 bedroom 2.5 bath built in 2007  (built as addition with full permits).

In other words you receive a 30% tax credit on the solar system as well as a 30% tax credit at the least on the roof that is under the solar system (full roof 30% depends on the advice of your CPA).Couple that with the roof now becoming a producing asset and offsetting the utility bill instead of a liability and the increase in appraised home value assuming the solar system is not leased then going solar makes a lot of sense at the same time as replacing/repairing a roof.

My big picture plans are to start an LLC soon and to, eventually, be a full time investor. 

Partner with people who have the same passions for providing great housing, helping fellow humans, and building a full and abundant life.

Maybe it’s foolish to think of acquiring all 12 but I’m ready to move on and do this full time.

Might be tougher to blame them for watching this if it got stopped up with leaves that were not their fault.Now if they stuffed a rag in the drain (in the lease or not) I would think they would be negligent and be responsible for this repair.Might be best to make this as idiot proof as humanly possible to prevent or minimize issues with this.Maybe also setup an inspection in the fall after leaves have fallen to check this specifically along with rest of property.

I work a full time job that pays about $15/hr. 

Yeah, Miami Beach in a full-on war on AirBnB.

Should I bring a self-prepared contract for the attorney to look over or give them the full autonomy of how the contract is designed (for both assignment and purchase/sale document)?

.--  Pursue art full time within the next 3-7 years.