Am I broken? Am I stuck? Do I have to return my audiophile card now?

I was in a similar quandary.

I'd gone back and forth between Devore and Joseph Audio speakers, ended up buying original Joseph Perspective speakers when they'd just come out with the new graphene version.  My idea was to eventually send them for the upgrade.

Over the years I had an "Audio fund" account where I'd put little bits of saved money but mostly if I sold any gear the money went in to that account for new gear.

I'd finally used up almost all the funds, and had sold my last bit of gear so...no more fun money to play with.   Then Devore came out with the O/baby and I was also considering grabbing those to have the Devore sound around "at hand."  Or, put the money in to some things I needed to upgrade for my home theater.

So the question was mostly whether to put that last bit of money, and it was still a substantial amount, to upgrading my speakers.    It was so easy to rationalize either way:  "The Perspectives already sound AMAZING.  What do I need the upgrade for?   Just use the money for an actually NEW speaker for the collection like the Devores, or finally friggin' do that HT upgrade you've been needing!"

At the same time I sort of saw the Josephs as my end-game speakers.  They were the most expensive speakers I've owned, and no way I'd be throwing any more money to upgrade to a different speaker.   So I wanted them to be "the best they can be."   I just knew that despite all the rationalization above about "they sound fine!" that...just being audiophile me...I'd continually wonder about how they would sound with the upgrade, so maybe just do that and call it quits.

So I decided to pay for the upgrade.  Result:  yes they sound amazing.   Way better?  Not necessarily, but still...wow.  But it does seem to have eradicated my upgrade itch.  They are as good as they can be, I used the strategy of "throwing money at it until I can't throw any more" so I don't even contemplate money going towards new speakers (or other gear).   I'm set...partially out of necessity.  And in that way it's sort of freeing :-)

@bigfatpaulie 

Throwing more money at a DAC or power cables/audio cables...?   Not what I'd suggest.  But, hey, we all have our opinions.

I fell in love with the sound of Devore O/96 speakers and was offered an in-home audition.  I abstained.  On major reason was that I may well have loved the sound of those in my room.  But in a way I didn't want that experience because I also knew they would be a harder fit aesthetically and ergonomically in my room, given it shares duty with home theater.  (Wide speakers like the Devores could encroach on my projection screen space behind my speakers).  So a bit of "better not go there."

Another area I have restrained myself is upgrading my home theater.  I've had a 4K capable projector for years, yet still haven't upgraded my source to 4K!  And I'm a home theater nut!   Unfortunately my system is complex enough that it would take upgrading all my video cables, and re-running new cabling through floors etc.  Now, if I were in Home Theater Upgrade mode that's something I probably would have done long ago.  But it's expensive and a hassle, and between the home theater and my music system, the money kept going to my music system.  I could always fall back on "the image I have is so bloody fantastic as it is, do I REALLY need to change it now?"

Now, since I've finally spent myself out on the music system, my HT is my next upgrade, when money permits.

Carpe Diem - If there is a deal there that allows you to do the move I would take it. Those opportunities don’t come up often.

Yes there is the "rare opportunity" thing, if that's the case.

I'm sure I'm not alone in still occasionally kicking myself in missing certain rare opportunities that are unlikely to come again.

And I've been extremely happy in TAKING rare opportunities that wouldn't come again.   For instance, I was always a fan of MBL omnis, which were way too expensive.  But I saw an add for a "rare opportunity to own MBL" in which an MBL speaker had been cosmetically damaged in shipping to a customer, and so it was being sold at less than 1/5 the price!  Even though I didn't have much money at the time, I stretched to grab those and was very glad I did.  I got to live with MBLs for a good 10 years!

Likewise, in years before a deal had fell through for a pair of Thiel 2.7 speakers in ebony.  I lusted after those things, loving the Thiel sound (I had big 3.7s I needed to replace) and LOVING the rare ebony finish that would match my decor.  I kicked myself for not getting those when they sold.   Thiel 2.7s were rare enough, but in ebony...super rare.  So when another pair finally came up years later I grabbed them.  So glad I did because they were everything I hoped, and just the right finish. And I've never seen them for sale since.

Then there are missed opportunities.  For instance I was gagga over some Waveform Mach Solo speakers that I once reviewed.  One of the best speakers I've heard in my home, in a gorgeous finish, but I let them go.  I thought about those speakers for years, and kept my eye on the used market.  But that model had been manufactured just when Waveform was going under, so they were essentially never on the used market.  About 17 years later a pair popped up for sale!  It was the last one Waveform ever built AND it was custom modded with better drivers by the manufacturer (was his own pair).  AND it was within driving distance local pick up.  AND it was at an INSANELY low price!   All perfect, right?  Except this occurred when I had a rare extended time out of work.  I just wasn't confident about spending any money at that moment, even though some work would eventually come.  So...I watched as they were eventually sold.  And...of course....work came not long after!    Still kicking myself....