Hello Loudog Dablog and welcome to BleepingComputer
Being in the construction management field I can identify with you seeing you been doing this for 22 years I would take a wild guess your around the same age as I +\- 2 or 3 years.
I have worked with contractors some very savvy with technology and some not. Todays Job supers and project managers are attending a 4 year college program they are trained on the latest and greatest software which gives them a huge advantage over those who have been in the field for better then 10 or so years who are trying to go back and get caught up with technology,,, Not as easy to go back and try and retain all the info while still trying to run a business and keep it productive and profitable.
Thats not to say some aren't picking it up quickly cause some are and just when you think you have a good handle on what the software can do someone shows you that there is a better way or easier way to perform a task... Oh and of course as you said the product itself is upgraded..
Have you ever seen the rush to fill them out the day they're due and the looks on their faces when they are trying to remember what it was they did and when?
It's even funnier watching the contractors trying to figure it out so they can explain it to the bookkeeper. The fact is, is, that most of the bad reputation contractors get in the industry is due by bad records, not poor work.
The way I see it for most of these guys they care about one thing the finish product
there is no greater feeling of pride then standing back and looking at a brand new house or a brand new building, stone wall whatever and saying to yourself thats my/our work right there with the greatest sense of accomplishment.
Now hop behind your laptop and put in your time and upon completion of getting all the info in a little window pops up and says Successfully entered
not quite the same rush.
While technology is becoming a necessity some will just continue to look beyond it and hope someone else will handle that side of it for them.
I have one very successful friend of mine who owns a paving business he is a work horse sun up till past sundown, He works harder then anyone on his crew leads by example,, If I need to get in touch with him I need to call his wife who in turn calls one of the guys working with him,,, He wont even carry a cell phone someone calling him would be cutting into his work time and if you do call him it better be for good reason!!!
I guess what I m trying to say is one needs to find their comfort level and step outside it some if they can if not look for some one they trust to handle the business side of things.
The other side of it I see is a building tech trying to work on a computer trying to close out calls or respond to e-mails to me thats a waste of time that will take them twice as long as an entry level person to do,,, If the tech wants to learn it great but most could care less,,,,,
Need to get back to work that coffee kick got me going
Best of luck to you