Out of those two, I usually take the second choice.
I also find myself buying the cheapest thing I want (i.e. If there are 3 skills I want costing 4,5 & 6 points each I'll almost always get them in that order.)
Starter Personas have always gotten a raw deal in my eyes. For something that's supposed to be the purest manifestation of your heart, you sure seem to ditch them pretty quick in favour of something you made by stapling a pixie to a rotten horse.
I only recently learned that Youtube does this too if you either make too many comments (which makes a sort of sense) on a particular video or edit a comment too many times (which really doesn't.)
As someone who has a bad habit of doing that second one, I suspect quite a few of my comments...
I quite liked how the Shadowrun Returns games do it: The loadouts of your party members auto-update as the story progresses without you having to do a thing, but you can still swap out one of their weapons or spells if there's something you really want in your team.