Season preference?
This is also an example of why I want to break up story telling like I am. Vacations (except mine) won't bring everything to a grinding halt.
Considering the vacation, maybe I should start with a late season (unless I'm misunderstanding your intent) like Autumn or Winter.
The season doesn't matter. What one magus does in the spring won't likely affect what happens in a later season. Your character's temperment has more to do with the decision of which season they'll manage.
The only impact I see your vacation as having is on holding the initial welcome council meeting where all this gets sorted out in character, and decisions as to which resources which magus expects to use. As long as we can determine your character's preferences now, and all the players agree to it, we can resolve the first council concurrent with the seasonal stories taking place. Does that make sense? This also makes getting the build points for covenant creation sorted out very important, too.
I can see your magus character getting called into multiple stories throughout the year, so you're one I had in mind for the annual advancement model. What do you think of that?
That would sound great.
As for Season preference then (since the vacation shouldn't impact it) Spring. He's a bit of a go-getter, I can see him arriving and starting right away to focus on making the place organized and defensible, it would be his initial priority.
I plan to be posting about once per day. As I think is normal for pbp, some days I'll have a lot of time and want to post heaps; other times I might have to miss a day. But basically 1/day sounds about right.
I'm in East Coast USA time-zone for the foreseeable future.
Thinking about the characters we have, it seems to me that it might be best to leave Iosephus till last, or nearly last - he has, as I've said, been living alone in a cave for most of the last three decades, and thus lacks any experience whatsoever in managing a large enterprise like a covenant, balancing the competing interests of others, dealing with grogs, and so forth. (And, let's face it, he's likely to be pretty bad at it, at least at first). So he's likely to be a better manager if he gets a chance to settle in first. That will be a big enough adjustment for him to start with, I think,
(Plus Apollodorus seems like a sensible, practical Jerbiton type who isn't going to be eager to turn his covenant over to the crazy Criamon right away, even just for a season. But maybe by the time six months or a year passes, Iosephus will have earned his stripes a little in that regard. Just a thought.)
All the other stuff you're saying about running all the seasons simultaneously, and then calculating xp at the end of the year, sounds good to me.
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Posting frequency: Prolly wont be able to post daily, the asked for "2-4 times per week" should not be a problem. How detailed those posts are gonna be if i participate in 5 different stories is another matter. So i will prolly refrain from playing a grog in every story and concentrate on my magus and my companion for a start to see how it goes.
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Location: Since my location is a bit cryptic i should elaborate: Mogontiacum is the roman name of Mainz, a state capital of germany.
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Covenant management: No preferences but right in the middle (autumn in the first year) seems to be still available so i take that.
Advancement like described sounds good to me!
Someone was going to have to sit out the first year. And your character is a prime one to do that. In years where a character doesn't manage the covenant for a season, I'll trigger story flaws. It's a bit artificial but...that's the best way to make it work. Since your story Criamon's story flaw is Visions, I can intertwine that as an excuse to have you get to know the covenant, and be ready to manage it come the spring of 1221.
Just throwing that one out there.
Sounds great to me!
I can almost always post probably multiple times a day. Work schedule is usually 4am to some time before noon, which gives my afternoons free. There may be times (like today) when I have to do all my posting at once, but that grates on me 
Northeastern Pennsylvania, USA
I don't have a "I have to rule during blah season" thing, but ideally I would like Fiona to manage the covenant during winter...I expect her to spend a good part of the first year (when she's not setting up her lab) getting her garden up and running...which would be planting, growing, and harvesting maybe.
I think we're getting close to starting. I know there might be a few companions missing, but that alright and can be sorted out overtime. If Mad Max has a factor, or whatever the Verditius term is for one who sells his magical items to the mundane world, it's certainly reasonable for him to come along later. Who's missing a companion and player for that companion? I'd like to kinda get that nailed down a bit. I know there's been PM'ing back and forth, but I'd like to have a listing of that.
As it is, we're just missing a few build points from a couple of people, and once I get those I'll be opening up a prelude thread (which might end up taking a long while due to qcipher's vacation) where the players can be introduced and we'll also begin the seasonal threads where the characters start to get to know the covenant.
If each player could list their Magus by name and then the name of their companion and player who's running that companion below, I'd appreciate it..
I don't have a companion yet for my magus and haven't started making a companion yet. I figured I'd be doing that today.
Player: Westerhaven
Magus: Iosephus ex Criamon
Magus' Companion: An as-yet nameless friend who connects Iosephus, the weird mystic, back to worldly things, sometimes in a rather troublesome fashion. Played by qcipher, if he still wants to role.
Companion: Shield-companion to Fiona ex Miscellanea. A highland swordsman, normal-sized but raised in a clan of giants. He actually serves Fiona's Giant patron, due to a curse.
Yes, I am making Iosephus's Companion, I'll send an IM in a bit with a bit more on what I'm thinking.
Magus: Fiona ex Miscellanea
Fiona's Companion: played by Jonah
Companion I'll be playing: Wilhelm the Woodsman, Companion to Silviatos
I'm not sure who was going to play my companion, though I pitched a decent idea.
By the bye, how many xp do our grogs & companions get for 1220? (And is it going to be a set amount every year, or does it vary?)
So 30 for those who are stated out. Any who went on adventure get their awarded adventure xp.
I'd like the new players to give serious thought to companions. Either companions to other Magi or companions who might be useful to the covenant.
And, we have a companion that's been abandoned by the player, Ivor[1], who is close to Fiona. If you think you'd like to give him a play, let someone know. Companions (and grogs) can be involved in multiple stories per year, if someone wants to play a character that much.
[1] Some things about Ivor can be reworked to suit the player taking him on. He should be beholden to the clan Fiona's from, though. Beyond that, I don't have an objection to him being retconned a bit.
Going ahead and updating the grogs I brought in, should I also update with 30 xp the teacher? He's statted out and could be used as a grog.
Yup, you put some initial work into him, and AFAIK, no one used him to teach. AFAIK, no one had him teach anything, I was using the teacher that was brought with and abandoned by Silviatos on Ulrich's behalf. If he does teacher two seasons equivalent, his XPs will actually go down, and so I need to revise this for professionals working for the covenant.