A FINAL NOTE
The latest SDA's update included a major revamping to the scripts. The author himself warmly recommended that the new version is used on a new game.
Much to my dismay, his recommendation fully applies to my save.
Being unable to play out DB the way I wanted, I've come to the (painful) conclusion that Straycat's tale has to end here.

Q: what the hell is this stuff?
A: this is a transcription of the journal I've been keeping during my last Skyrim playthrough. Started off as a pretty simple text file to keep track of the stuff I had been doing, it quickly escalated to a full-fledged diary where I would "decorate" every in-game event to match my roleplaying - as I've already said, I don't think Bethesda had me in mind when they designed this game.

Q: what does your playthrough cover?
A: well, a lot of stuff actually. Many miscellaneous quests (such as Morvath's quest in Morthal, a few daedric quests, the Wolf Queen); big quests added by mods (Moonpath to Elsweyr, Beyond Reach, Falskaar, Wyrmstooth - and perhaps others I forgot); and of course Dawnguard and the main quest. Didn't bother with the Companions, or the Thieves Guild. And, I destroyed the Dark Brotherhood. My character is a good guy who hates furries does not want to be associated with any guild.

Q: why bother with keeping a diary?
A: as I said, at first it was just a Skyrim equivalent to a post-it. Then it just became funny. Do you remember that "I don't think Bethesda etc." line above? Well keeping a journal and using it to add "my own personal taste" to the game almost completely filled the gap. I would pick the dialogue choice that most closely fit my character (roleplaying-wise) and then I would record the event by turning a two-lines dialogue into something epic, or funny, or whatever. In a very straightforward way I can say that,
"Skyrim + this diary = my Skyrim"
Sounds pretentious?

Q: hey, it's HUGE! Do you really expect me to read through all of this nonsense?!
A: if my scope was to appease a large audience I would have probably given up after the first two pages.
Plus, didn't I tell you I'm verbose?

Q: TL;DR. What happens?
A: my character starts off as a cynical bastard with a difficult past, then things happen and he ends up saving the world, becoming a hero and marrying a cute vampire princess.

Q: wait... you get to Fus Ro Dah peope before talking to the greybeards! How come?!
A: I cheated!
... Well, not really.
A couple mods required me to be "officially" recognised as DB by the old bags on the mountain Greybeards so I might have happened to... uh, re-arrange the chronological order of certain events to better fit my idea of how things were to play out (roleplaying-wise, that is).

Q: lots of typos here...
A: seriously, my heart aches at that. English's not my native language, and while I'm pretty good when it comes to technical English (been working for a engineering company where I used English 90% of the time for many years) I'm not that good at "everyday" English. Plus most of my writing takes place at night when I'm, uh, less than perfectly aware of what I'm doing. I happen to do some grammar and spelling check every now and then so the quality of my prose is going to increase however I already know my learning curve is going to show a strictly asymptotical, rather than linear behaviour.
Do let me know if you find an error by the way!

Q: any plan for the future?
A: as soon as Serana Dialogue AddOn covers Dragonborn's main quest I'm going to skim through that. Since when I discovered SDA I've been keeping Serana as a full-time partner (she's sexy, she's funny, she's teasing,... did I already mention she's sexy?), and I want her to comment on Solstheim and the stuff that's going to happen there. Then I'll most likely - like, 99.9% certain - stop.

Q: Ah! Found you! You've installed a sex mod! You perverted freak!
A: who doesn't?

Q: me!
A: really?

Q: what are you doing in the meantime?
A: I'm trying to learn the basics of the Creation Kit to add a few dialogue lines - if the outcome is nice enough I might even consider uploading some stuff on the Nexus (I consider such possibility to be extremely unlikely, still...).
It should be relatively easy - once I learn how to do that, of course.

Q: why not adding {your mod name here} to your playthrough? It's cool!
A: I want to dedicate myself to other stuff (nothing serious of course. That would be denying my true self!).
Plus, I feel my playthrough's closing to a satisfying end. Once I kick Hermaeus Mora's ass back into Oblivion my character is likely going to call it a day and fulfill the promise he made to Serana to explore Tamriel together (read the previous poin in case you're wondering when and where the DB made such a promise). Still unsure whether turning him into a vampire (most unlikely), turning Serana back into a mortal (something I might want to explore) or keep things as they are (would not be satisfying but might be the easiest way to wrap things up).
If I ever happen to again feel the urge to explore the cold lands of Skyrim I might consider your suggestion. Still, it's unlikely (and I mean: UNLIKELY) that I'll ever go through all the trouble of writing a journal of my playthrough (which I'll most likely do) AND publishing it online.

Q: best mod you'd recommend?
A: now that's a difficult question. In my view, any mod that turns Skyrim into a survivalist experience is a must.
When it comes to additional content I'd say that Beyond Reach is the mod that hit me the most (straight into the stomach to be honest). I had a hard time at finding a way to get my character out of the shell-shock syndrome that mod induced, and I'm still not satisfied with the things I wrote down.
Seriously, to me that mod is Skyrim's equivalent to Heart of Darkness.

Q: you used an iframe! Shame on you!
A: ehehehe I tried messing with divs and dynamically loading content inside them. Things worked nicely but then I faced a couple issues and rather than delving into the matter I opted for the quick dirty way.
I'm one lazy guy and I'm not afraid to admit it =P!