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Worst VPS/DS Experience?

I haven't had any bad experiences while running a VPS or a dedicated server. Most of the companies that I've used were pretty good over the years. I've been fortunate enough that I've had reliable and quality providers.
 
I have to agree with @Cpvr. I generally research a hosting provider (VPS or dedicated) heavily before I decide to go with it, and if they happen to get bought out by EIG start quickly looking for another to replace them. EIG=KOD (kiss of death).
 
I had a bad experience trying to move from VPS to a Dedicated Server.

However, it was really my fault to begin with.

I unknowingly thought that I would be better off moving to a DS than upgrading my VPS.

The DS looked better and would have been had I not had so many websites on it sucking down it's resources.

Needless to say, the hosting company did me right and even though they didn't have to, they gave me a 6-month credit after getting me on the right VPS plan and back online. It's one of the reasons I've stayed with them for nearly 20 years now.
 
I unknowingly thought that I would be better off moving to a DS than upgrading my VPS.
Generally a move to a dedicated from a VPS will be an upgrade. There are rare instances where that might not be true... say moving from a VPS that has "real" server level hardware to what amounts to a desktop unit provisioned as a dedicated server (and I see a LOT of those).
That is why you really need to look at the hardware that the dedicated server is using. I don't mind using even a 5-8 year old CPU as long as it was a true server designed CPU as it will still work well for most lower to mid level uses for sites.
 
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