When do you upgrade kayaks?

When do you upgrade kayaks.... Hummm... Whenever you CAN!    They call it the madness for a reason, and many of us have taken the plunge on several over time.  Your needs might change, you might want something easier to carry, or something that is more comfortable for longer outings, or trolling.  Whatever the case is, you might end up with a 'quiver' of kayaks for different uses.  You have been warned 

We were also told to use condoms.... No coming back from the madness

I love the outback.  To me its the perfect balance for the NorCal coast, and likely many other places.  You want something long enough to have speed, stable enough to be safe in the ocean and carrying gear (FF, crab pots, downrigger, 50 lbs of salmon, etc), the newer (2019+) design is better as it really cuts through swells and wavelets without losing speed, transducer well can accommodate side scan, rudder system almost bullet proof, the seat is very comfortable and adjustable (I recommend setting as low as possible to lower the CG and have the kayak even more stable.  And the kayak must be manageable for one person, including transportation, hauling to the water (get the biggest Hobie wheels not the smaller ones), etc.  Its nice to have a kayak where you are dependent on help from others.  There is even a nifty bungie cord system for getting the Hobie wheels in proper position under the kayak by yourself.
There's a reason where I fish, 70% of the kayaks are outbacks. 

In 2008 I got a Hobie Revo. Never looked at another kayak.
Still use it to this day.

The Compass is a great boat although I wish they had stayed with a twist and stow rudder. I have a 2012 Revo and a Compass. The Compass has become my primary boat for Ocean fishing.
Pedal yaks are IMO superior for trolling. However if you are rockfishing from small Sonoma coast spots, also having a paddle yak for beach launches could be a good thing.
Getting a Pro Angler down to a beach and then launched is a heck of a lot of work. It's more of a Harbor or lake boat