BTW, I consider contingencies property-related emergencies, not "I'm so stressed, let's go on vacation."

Perhaps they can patch it and resurface it for a modest investment and make it look fairly nice for a cheap price (relative to other options).

@Mike Dymski  I look at this as   Over paying relative to what ???? 

Having a PMP and Lean Six Sigma Black Belt certification have helped me create a process-oriented approach to executing strategy and analyzing data to prioritize initiatives as well as course correct well before issues become catastrophic.

what other legal related things do I need to do?

First, tell you boss at your company and make sure it's okay -- it doesn't do any good to make an investor mentor if you also lose your 9-to-5.As for approaching the individual: 1) explain why you're interested; 2) say that you did get the ok from your company, and that you're doing it in a totally private not-related-to-your-company way; and 3) offer to help out with his properties like you said.A key thing to be clear about -- if you offer to do any of your professional day-job work for him on the side as a favor for him helping you out, you need to be sure that your company doesn't mind you doing it.

Try to do it in a city that has a 3rd party relative or a friend that is local of the subject property that will help you out and reduce your travel expenses down.I would normally tell you to be honest with the seller except from when you are Wholesaling and assigning the contract. 

These are all questions whose answers will help you chart the way forward ... there is no one size fits all answer.From an operational perspective it is always pleasant to know that your building envelope is relatively efficient (insulated and air sealed); that building systems (electrical, plumbing, HVAC and communications are up-to-date and dependable) and that you have the ability to put accountability for resource consumption in the hands of the tenants.  

I am looking to invest in a residential rental property in Jax and was wondering if anyone has a mortgage broker they recommend or an experience worth sharing in relation to finding the best commercial loan rates? 

Now admittedly I had a small sample size over just a few years but tenant relations are generally much better.I get paid on time every month.If a tenant breaks something, they have to fix it or  lose their section 8.There is a lack of supply it seems so tenants jump on vacancy's and stay put.