One important question I have not seen asked, or maybe it was and I missed it: Is the investment you are thinking of local to you or far away.If it is local, then roll your sleeves up and jump in.

In the meantime, roll up your sleeves and get to work getting some hands on experience.

He knew that I had no tricks or games up my sleeve.

Who knows, this guy has many tricks up his sleeve. 

For many homes like this the have metal boxes for the outlets/switches with I believe it is called Romex wire (wire inside a flex metal sleeve) which is fastened to the metal outlet box as well as breaker box.

There are digital ways to handle but a way to deal with hard copy cards (perhaps with notes on them) is to get plastic sleeves that fit in a three ring binder.

Asking for help and advice is foreign to me since I usually just roll up my sleeves and go with the trial and error method.

Book smarts make dinner conversation; street smarts make money.Roll up your sleeves, get off the internet and get out in the street.  

Now time to roll up my sleeves....Let me know if I can offer any advise or assistance.Zach 

If they aren't 'roll up their sleeves' type of people, then there's going to be concerned about your decision and ability to handle it.