It sounds like you've already thought through a lot of it. One more thing as an addendum to the versatility aspect...The Model 29 will have much heavier bullets available. If you like shooting 300 grain bullets and such, then the Model 29 is the way. It sounds like you're more into old school type stuff since you say you might buy a 24 or 25 under the right circumstances, so it sounds like you might want to try the model 57.

I've owned a ton of model 29's but only one 57. I wish I had the 57 back. Of course I've already got a 629 so...