I also heard you state in your letter that you have been asked to visit his apt. several times (repeatedly) in the past several months.

I believe BP serves the Kool-Aid in several different flavors.

I own several rental properties in the Cleveland Area and I also own a local insurance agency.

If you are doing it in excel - a receipt for $100 that consisted of $25 paint, $25 tools, $50 roof supplies.can be entered into excel like$25 paint$25 tools$50 roof suppliesAt the end of the year you can sum up all the costs by description and provide that to your accountant.A couple things to point outWhether you expense an item or capitalize it will depend on several factors such as if you are increasing the useful life of the item, making it ready for a different use or making it more efficient.

Or even several people, which I'm sure will come with a solid deal so I'm not asking for that necessarily..

The technology really has expanded over the past several years....take advantage of it. 

Yeah, I have received several quotes. 

If you can't put them on separate meters, I've seen several BP posts where the landlord charged the tenants a "utility fee" each month to recoup the cost. 

The training to become a land surveyor seems fairly minimal and surveys cost at least several hundred dollars for a few hours work.

I have started my real estate education by listening to BiggerPockets podcast, reading posted articles, and I have purchased and started reading  several of the BiggerPockets real estate books.