What wears most on the points is the rubbing block. As it wears the point gap changes. Another wear spot is the contact surfaces. They will deteriorate over time which also changes the gap. Regular engine operation is good to keep the point contacts from corroding which can get to the point where they don't conduct.
I have a point burnishing tool but only use it when the points don't conduct. If I do feel the need to clean a working set of contacts I'll drag a piece of stout paper through the closed contacts a couple times. The spring tension is enough force to clean them up. If theres a ridge or dish worn in the contacts replace them. The burnishing tool can clean them up enough to get you home.
Spring tension can also wear but that takes along time.
I've got some point/condenser engines that haven't had their points changed in over 5 years. I check the gap at every oil change and adjust as necessary but as long as they hold their gap fairly well and the dwell is within spec I'll run 'em until they start giving trouble, i.e. need constant adjustment, intermittent ignition problems, worn contact surfaces, etc.
Plugs are another story as they live in a very hostile environment and get checked more often and either cleaned/changed as necessary.
I like the vacuum method for setting the carbs and also use it for timing but I'm getting to where I like setting the timing via max advance at 3K rpm. If you have an adjustable timing light, set TDC to 35 degrees advanced with vacuum disconnected and plugged. With the vacuum connected it may read near 40 degrees at 3K rpm.
With this method you will more likely read a lot higher idle advance which is fine. But if the engine pings under load going up hill you may need to back it off a little.
Oddly, my stock 49 216's timing is just about spot on the BB when I use both the vacuum or max rpm method. My 54 235 is another story.....
Anyways, with these old engines that are either modified or bored or with different carb(s), exhausts etc, just another option/opinion to give them the coon tune

Dave