Dracaena White Stripe I think. It's pretty much par for the course for these. Brown tips without a yellow fringe are not overwatering. If anything it looks a little dry to me?

The slight stippling on the left hand leaf in the penultimate pic looks almost like cold or spray damage, but I can't be sure.

Doubtful about the cold/spray damage (I'm in sunny southern california). I've been careful not to over/under water, and I'm pretty sure this isn't a disease. Could this be an issue with the roots?

Do you have city water? I had a boss at the nursery I worked in tell me once that Dracenas don't like perlite.

I do use tap water. Can fluoride/chlorine do this to dracaenas? I haven't used perlite in my potting mix, as far as I can remember.

The damage does fit with fluoride toxicity. How long since it was repotted?

Just about a year ago

Was it potted-up or repotted (root trim & remove all old soil?) Looks like a "self-watering" pot?

it was potted up and repotted as well (new larger pot, and soil exchange). It is now in a self-watering pot, but I water from the top since I was advised not to use the bottom self-watering part of the pot.

I'm going to start using only distilled now. Hopefully that will improve things because I really can't see any other cause for this continual yellowing and dying all over.

How do you water your plant? Do you saturate the soil or just give it sips? Do you allow the water to run off after watering? When was the last time you took it to the shower to get a good soak? Fluoride does cause burned tips BUT if you are not properly watering it could mean it's getting burned from salts in the soil already. Take it to the shower and give it a good drench, then return it. Cut off the brown tips at an angle because they are not pretty but do not cut off the whole leave. The plant will withdraw the nutrients from the leaves as they dry and die. This is a normal wintertime activity because it also means the plant is not getting enough light and it is slowing down. I'd also move it closer to a south facing window, if you don't have a south facing window, out it in front of a West or East window. Not to the side of the window, in front of. See if that doesn't help your plant.

Thanks for the tips. It has been dying like this from summer to fall. So I don't think it's seasonal. I give it a good soak from the top every two weeks around this time of year (one week in the summer), but I make sure the soil is completely dry between waterings. The pot may collect excess water in the bottom, but I haven't checked. I will do that from now on. I'll try the shower idea in the mean time.

Drying completely is really stressful for non-cactus plants. The only time that happens to mine is if I've forgotten one or the once-a-week plan I use while plants are inside for winter isn't often enough for one. Some are in unheated rooms. If the soil doesn't rot roots when moist, the confounding tactic of trying to know when the soil is almost but not yet dry enough to damage a plant, and waiting until that point to give more water, is unnecessary. If one wants a Dracaena to maintain as many leaves as possible, letting it get too dry should be avoided.

Chlorine which I was told could cause similar problems dissipates if you let the water sit out 24 hours.

That advice is leftover from a time when most municipalities used a form of chlorination that could evaporate. Now most don't. Fluoride and lime also can't evaporate. Whenever possible, try to catch some rain or use distilled or condensate
from a dehumidifier or A/C for Dracaena plants in particular.