Goodies just arrived...
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Looks like we have bought them all - out of stock now 
That's usually what I do too. There is usually sufficient change between major OS upgrades to warrant a clean start.
However, not always so easy and that's the one potential downside of consolidating my 3 Pi's to a single laptop server.
As an aside, I recently upgraded my daily-driver PC 3 times. Once for an extra 16GB RAM, once for Windows 10 to Windows 11 and once for the addition of a 2nd 1TB drive. Windows often seems to get less stable after a major upgrade and that was true in 2 out of the 3 recent occasions. The exception being the drive addition which seems to have set everything back on an even keel and even seems to have sped things up a fair bit. I suspect drive 1 was probably getting too full NTFS really doesn't like getting more than around 80% full.
You have already probably considered this, but I will mention it just in case. If you have an extra drive, it's convenient to put the old one aside for a while you set up the new install. That way, if things go sideways, you can be back up and running with your old install in minutes or copy out some files you forgot in your initial selection of backup files.
Alternatively, you could take an image of the drive as a backup, but it's very convenient to have your old drive ready to go.
It also sounds like you have a lot of Pis sitting around your house for streaming audio, so maybe consider doing the install/upgrade on one of those devices instead so you can keep your working server up until the new one is up and stable. Once your new machine is up, you can put the old one where the "borrowed" one was.
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I'll be interested to see how you got on using the EasyUlt enclosure. I too have one and have had no success using it (with enclosed PNY SSD)
I have loaded drive with Buster and it will not boot.
In fact if I boot from SD card and then just plug in the drive I immediately lose SSH connection to the PI.
I have loaded drive with Buster and it will not boot.
Interestingly I resurrected an ancient 60G drive in an enclosure and it works perfectly.
I have read somewhere that not all drive interfaces play ball with the PI.
I had no success with it (put the SSD in the case and plugged it in to a USB socket on my PC) - then realised... "Oh silly boy - I need to initialise and format the SSD". Worked fine then.
This is one of the things I do very rarely, so always forget the basic steps (old age thing).
Yes I did that too.... but now clone your existing SDcard to it or load up buster\bullseye and see if the PI will boot from it.
I did read about some adapters not working well with the Pi4.
If you do have problems, I have used a couple of the adapters I linked earlier without issues.
Just looked and seen the PNY CS900 120GB SSD is currently GBP 5.99. Cheaper than an SD card!!
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