It is not a waste of time. Some of us study how people learn and perceive, so this is kind of a laboratory for us. And you are learning what people need to know in order to help you.
Don't feel bad about "doing it every day". I can't get my Office 365 to attach a file at work, so I have to send the file to myself using a different e-mail and then finish the job at home. The tech guys are so backed up doing other critical stuff I haven't bothered them, since I will be vacating this office in 2 months. It will be your turn in a year to help out the newbies. You should have seen me at the Family History center last night. I'm sure they thought I was a flaky old lady instead of someone whose been computing for over 40 years. I couldn't find anything on first try.
Sometimes your own security settings prevent you from saving the file. If that's the case, you can use Ancestry's e-mail option, send the information to one of us (date, ship, image number of however many, line number, etc.) and we can attach it like I did here. My e-mail is firstname.lastname@example.org
if you have trouble using the messaging service in Ancestry (you just click on the person's name to get into it.)