Selfhosted

As long as updates work between any two versions, or there's a clear upgrade path, I don't really care. I don't update my services on any particular schedule, so it doesn't matter much to me.

However, you should have a mechanism to inform users of important updates, like patches to known exploits. Don't spam me, but a nudge if I'm outside of some support window will probably get me to upgrade.

My upgrade cadence is probably every 3-6 months. I'll do system upgrades more often, but I try to avoid breaking my docker stuff.

I personally prefer consistent and smaller releases. It offers less opportunity for big bugs to creep in along with smaller fixes and features.

I saw agile mentioned here but here’s another suggestion. Agile can be helpful in the right situations but for solo devs/tiny teams, I really recommend looking into Basecamps “Shape Up” method. It uses longer cycles vs shorter sprints with a cool down period in between.

So in the case of OP, they could set a 6 week cycle and plan for things that can definitely be completed during that time period. Right at the end of the cycle you release. The goal is to finish before the cooldown to give yourself time to breathe and plan what to do for your next cycle. Play around with a fun feature, learn about a new tool or technique you wanna try, organizing your backlog, etc. You don’t want to spill tasks into the cooldown. Else it’s not a cooldown.

The online version of the Shape Up book is free and can be found here.

I prefer rarer, bigger, more tested updates, since I don't pull the updated docker containers that regularly.

I've been maintaining multiple release channels for most of my projects. I always have a nightly build and a dev build that I run manually or on every push. Actually versioned releases either happen directly after completing a milestone or when the release schedule calls for it.

Security and bugfixes, after one or two rounds of testing by early adopters/key users. Preferably through some form of automatic updates.

New features and breaking changes, or anything that requires the end-user to pay attention, I'd say no more than 4 times a year, and using a non-automatic form of update. The hard thing is getting the user's attention on the changes, and not just clicking next and then having a broken or insecure installation.

Most of my updates are automated so I don't even notice. Release whenever you think it's appropriate. Fixed a typo? Not worth a release. Critical security issue? Release immediately.

My background is in enterprise software, so that is obviously different than a desktop tool for individual use, but it informs my opinions.

In general it depends on the use (is it "production" critical, etc) as well as the update and distribution mechanisms.

I have several (mostly for windows) FOSS projects i have stopped using or just rarely update because they require too many steps to update, and/or do so too often.Or they require a reboot. Some of them prompt for an update every time I start them. Feh.

That said, if there isn't much friction like testing cycles or manual steps to update, I want faster updates.

Most of my self-hosted stuff falls into the category of getting updates via package managers or docker. Those are often seemless and do not require manual steps.

Less releases with more testing. I normally wait some time before upgrading (no matter the application) as I prefer stability over extra/new features that I may use or not.

This isn't something that should really be set by users of an app. It should be set by you, as you will be the one to handle user feedback and bug reports.

That being said, bigger releases are a challenge from a debugging report standpoint because you are introducing many more changes in each release compared to a smaller number of charges in more frequent releases. This is why many devops teams in corporate land try to keep releases smaller and more frequent (see also: Agile Development)