I inherited a box of reel-to-reel tapes among all the other bits and pieces when my dad died. I'm going through them slowly, trying to see what is on some of them and what might be worth getting someone to digitise properly.
I have a tape player, but it's old and unreliable, it doesn't play back consistently, it sometimes refuses to fast forward or rewind, and the line outputs sometimes just give up. It's good enough to find out what's there, but I also don't want to be babysitting a machine while it chugs through transferring analog to digital in real time. Also, of course, it's fun to get old machines working. Oh, but on the other hand, I don't really know what I'm doing most of the time :)
So I'm approaching the point where I just get some quotes for someone to do the whole job with professional equipment and professional expertise. It will be fun enough to go through and listen to the finished files without having to do the donkey work.