I’m a self-proclaimed nostalgia sap. I love looking at old photos and reminiscing about the past. As such, I have a strong desire to get all of our old photos digitized. 
We have thousands, literally. And I’d like to get them into our iPhoto library, next to all the digital photos we have from the more recent past.
Scanning them all, one by one, takes a lot of time. For instance, it took me about 3 minutes to scan in today’s photo, which was taken in Olympia, WA on January 1, 1991, the day after Melinda and I were married. We went to Olympia to announce to some close friends that we had gotten married (a surprise to everyone but Melinda and me). I’m very pleased to have a digital version of this picture. Like I said, it took me about 3 minutes to get it.
But thousands of pictures at 3 minutes each is thousands of minutes of my time. I could pay $200 to have 1000 pictures digitized and put on a DVD.
Should I do that?
Today’s Question: What are things you know how to do but pay to have someone else do them for you?
Andy Smallman 
Do it! You will be so happy to have it all when you reach my age. And then you can keep up with it from now on.
I can’t believe how young you two look in that picture. I remember thinking you were quite mature when you married.
I’m a total nostalgia sap too (I didn’t realize you were one! Let it never be said that one can’t learn something from Chat with Andy :P), and I have a bazillion photos that also need to be digitized. Unfortunately, all the scanners I’ve gotten (and eventually discarded or lost the power cord for) over the years have resulted in really sub-optimal scans. So I intend to, one of these days, pay someone to scan them for me and (I hope/expect) produce really top-notch images. Ditto with the box with about 40 8mm tapes, that are probably fading just a bit more even as I type this. 😦 The only question is when I will finally get around to sending them in.
To be honest that is my deciding factor: if I can do it myself I don’t pay someone else to do it. There are enough things I don’t have the knowledge or right tools to do.
After forty seven years of cleaning my own house, I recently started paying someone to clean it about every three weeks. I have always resented house cleaning as it is a very repetitive chore, a thankless task which has always fallen to me — yes, I lived in the generation where the woman did it all while the man was away at work all day.
When we were both retired, my husband took over the sweeping which led to many problems as I waited for him to complete his task. There is so much less friction in our household now and I have a clean house ALL the time because I can now devote myself to “picking up.”
I have always had a very hard time spending money on things I can do myself. Being from a generation raised after the Depression, I learned frugality and perhaps even “stinginess.” I am really thankful that I can afford to pay someone to do the work, but I am much more thankful that I got over my hangups about paying someone to do work I can do. Why else do we have money than to use it to make our lives easier or more enjoyable? For the first sixty years of my life, money was for the latter but in the next however many years I have left, it is obvious it will be to make life easier.