Contractors and technology

It seems that contractors and technology do not mix.  There have been several threads on Bigger Pockets in the past about finding good contractors, working with contractors, and communicating with contractors.

What I have found in dealing with contractors is that they may be good at their trades, but horrible at keeping paperwork, billing, and technology in general.  Many contractors I work with still hand-write estimates and invoices.

A few examples:

I was getting some foundation work done. The foundation contractor had an iPad with him, and was showing me images of prior work that the company had done.  Having an iPad, I thought he seemed pretty technologically advanced.  He mentioned that he had gotten the iPad recently.  But then he pulls out his paper estimate pad and writes me up an estimate.  I agree to it, and so he had to pull out his paper invoice pad and write me up an estimate.

I had some drain cleaning done on 4/20 at one of my properties.  I finally got the handwritten invoice in the mail about a month later.

Just the other day, I was getting some carpet work quoted.  The guy gave me a verbal quote and I asked for a written quote emailed to me.  The contractor told me that he wasn't very good with "computers" and that he'd have to get me the estimate when he got home to his desktop.  Okay, that's fine.  But then I get the email. What he did was type up the estimate in his Quickbooks, print off an estimate, then take a picture of it with his smartphone and email me the picture of the piece of paper!

Ah, contractors!