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 :-)