I used to carry an Uncle Henry stockman on the farm, which sounds like it would basically be a stainless equivalent of the OP's Old Timer. I carried it to school and such daily for a couple years before the newness wore off and I turned it into a full fledged "farm knife", and then carried if for a couple/3 years more.
I was never really happy with how soft the steel was. (I believe the carbon versions are harder?) The edge would roll and get dinged readily when doing the sort of stuff a knife was normally called upon to do around the farm. But, I carried it anyway, and just sharpened out damage as it occured. The shape of main clip point blade and sheepsfoot blade had changed noticeably by the end. To its credit it never really loosened up, but it did have trouble with galling where the tangs rubbed against the springs. I finally did some grinding on it to improve the swedges to provide more clearance for the blades to close, and after I'd sharpened it significantly to where the edges were getting to thick for my liking, I reground the primary grinds on the sheepsfoot and spey blades.
Finally one day the thing must have fallen out of my pocket on the driveway, and it got ran over by the tractors a bunch before Dad found it back. The liners & pins got bent to the point the blades don't open and close freely any more, so I retired it from service. I still keep it on my workbench for cutting stuff I don't want to waste a better edge on. So in all, I really loved the versatility provided by the 3 different blade shapes and edge profiles, but wished it was harder, had thinner grinds, and had a little better execution in design. FWIW.