Always upgrade WordPress?

You make a really good point here. I don't think you should avoid updating the wordpress core - mainly because of security issues. Having a site hacked is no fun at all!

When a plugin becomes incompatible then it means it's time to either find a new plugin, fix the incompatible plugin, or write your own.

Just because wordpress reports that a plugin has not been tested with an updated version of the wordpress core, doesn't necessarily mean that it is incompatible.

Unfortunately incompatibility presents itself as a bug that needs to be fixed as soon as possible.

I will only install plugins that are needed at the time. This stops any frontend code-bloat as well as cuts down on the chance of conflicts between plugins.

As far as redesigning a site - might be good to try and keep functionality and look-and-feel separate. This can be tricky to do when theme files are edited directly, but with a bit of planning, the code can be abstracted to a functions file.

I am confused by your questions... because they are not logical

Upgrading and re-designing have NOTHING to do with each other!

So, let's try to address your issues as separate topics.

Upgrade. I posted several times: when a major version is out (like 1.5 or 3.4) I always wait a few days (couple of weeks) because despite the best intentions there always will be some bugs. Soon a "bigfix" minor upgrade (like 1.5.1 or 3.4.1) will be out. That's my preferred time for upgrade.

However, when out of the blue there is a security update (1.5.3 or a similarly named version) - I will proceed immediately.

Plugins. I am known as a 'plugin minimalist'. Only beginners and ignorant users think there is a "must have" plugin list. There isn't. Use only plugins for additional features that can not be solved with any other method. Use plugins only for features that are a MUST for the purposes of your blog, its goals and functionality. Never because Jones also has it

And as it was said: if a plugin becomes incompatible, "poke" the author to update it or try to find a coder to update it for you or find another solution...

Design. "Design" in my books is the visible layer, the presentation of your data - in the WP world it's called theme. Since the same blog can switch form one theme to another, without losing any content, it is obvious the different components of a WP site are not related to each other in the way you implied in your OP.

A WP version upgrade doesn't request a "complete re-design" of the site. If it does... there was a problem with it from the start.
Just to reiterate as a reminder: any WP powered site has the following main components:
- the engine = the WP script itself, a.k.a. the core files having version numbers 1.0.... 3.4 etc.
- the content = stored in the MySQL database
- the presentation = design > theme

One can manipulate any of these components without messing the other two

Thanks Warriors - I appreciate the feedback. I guess I need to consider using less plugins & keep upgrading to keep up with security updates.

Kind regards to all!

Randall

Like Istvan says, you need to see them as 2 seperate things. If you want to use WP you need to upgrade - no way round without many issues following.
If you choose to use plugins = do so knowing they may become obsolete and you have no control over when..

I always upgrade as soon as it comes out, since they are more robust and secure than previous versions. Staying behind will some day cause you with down time and so the money.

I agree there really isn't a way around the upgrades. That being said you should have more than just occasional "complete re-designs" of each site. You should be backing up your site at least once a week anyway so just take a few minutes to do the minor updating of plugins, etc right after.

Just make sure you have everything backed up before you do the upgrades, copying everything from the file manager doesn't backup your databases which are just as vital for your site to run. There is yet another plugin that backup your databases automatically.

And if you are testing out what is working and what isn't make those changes when you do more extensive changes during a "re-design" session once a month or once a quarter.

Just my thoughts