I think the title says it all... Thanks to anyone who responds!

Yes, season++ simply applies to the season server / season characters, and the permanent changes apply to everything. So yes, you benefit from it too even if you started your season char before.

I had a lvl 60 season char from when Dosa came out and i logged in and it gave me the full set of tet boss gear.

on a side note the new player welfare in this game seems like a huge turn off.  The end game has become trash-tier in every regard, so why rush people into it?

If I was given BIS weapon upon logging into an mmorpg I  would probably immediately uninstall.  With such extreme levels of welfare you know they don't care much about the veteran and are chasing that new player dollar.

It's a good point, and I don't play enough to have a valid opinion about this, but though you get a lot of good gear from the beginning I feel like there are whole new levels of good gear which are still unattainable for new players or casual players like me.

I am spamming Seasons in order to get a decent set of gear and accessories for all my characters, but even when I pile all the best accessories and gear I got as reward at one point or another in one single character, the most I get is 260GS, which isn't even enough to approach most of the new content. 

So I guess in a way they balanced it by raising the average GS

thanks for the response anyway!

Oh, I haven't opened the Blackstar boxes yet so I guess once I add them to the Chosen Character who gets all the good gear it'll be closer to 270GS, but still...