Hobie PA12 Up-graders from an Outback, any regrets?

[IN2DEEP]

Hi guys, looking to get my first kayak. Also, currently a boat owner
Will be using mainly for SW inshore fishing (harbors, kelp beds, etc.), FW lake fishing and occasional exercise.
Unsure if I will be surf launching in the future
Pretty set that it will be a Hobie with the Mirage drive.
Either the PA12 or an Outback
Have two buddies with the PA12 and no complaints (their 1st. kayaks also)
I will be transporting with a LB pick-up w/camper shell.
Have the funds to get either one (used)
If I stay with it, I might end up with two so the GF or friends can join me.

Any PA12 up-graders that preferred their Outbacks?

If you tell me to get both, which one should I get first?

Thanks!