Alright I bought this DLC like two months ago but I've been putting off playing it because once I beat it I'm afraid I might be done with Skyrim for at least the immediate future. I've been finishing off side quests, uncompleted faction storylines, side characters on other save files,

exploring etc etc. I think I'm finally ready to write the last chapter of the Dragonborn before he hangs up his blades above the mantle and settles down for the nice quiet life at Lakeview manor.

Anything else I should do before I leave for Solstheim?

I've got my Legendary Daedric armor and weapons and the difficulty finally maxed out to legendary. I assume "Dragonborn" will have it's own set of characters and stories so their will be no need to take a follower? (Don't know if it would let me?... although I really have no idea as I've been staying away from all synopisis as to avoid spoilers.)

The only pre-requisites I like to do is do the main quest, have a level above 40, and have all the Dragon Priest masks. Also have a nice bank of Dragon souls.

You sound like you're ready.

Ah of course, it hadn't even occurred to me that the DLC might have new T'hums

A cursory glance at my magic menu says I've got 23 souls so at least I should be covered in that department.

I've got a few dragon masks laying here and there about the ol' homestead, but I never really made a point of tracking them down. Is there a benefit or some side story to collecting them all? (or taking them with you for that matter?)

Besides the preequisite for completing the start of the Skyrim Main Quest.... You should be at least level 25-30.

Other than that, just get in and explore. Stop worrying about gear/weapons and just explore

Funny story.... I made a big show of going down to the cellar collecting my best armor and weapons (which I had collecting dust on on their respective places of storage while I finished up other businesses Skyrim), said goodbyes to the family (collecting every last bit of coin the store made), read the note gotten off the two cultists one last time to set the mood, took two steps out the front door.............and got promptly eaten by an Elder Dragon sitting on top of the house.

Yep. There are 4 new shouts, so you're fine.