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In my current replay of Oblivion, I've decided to more or less complete each faction's questline before going on to another faction. So far I haven't followed this strictly, because I did join the Thieves Guild and Mages Guild and Fighters Guild before completing the Arena questline. But I'd like to wrap up the Arena questline before going any further with the other factions, except I'm not sure whether it's safe to complete the Origin of the Gray Prince yet. I've already done the quest, I just haven't given the diary to the Gray Prince yet.

If I complete the Origin of the Gray Prince and am awarded the Gray Prince's Training, but haven't already leveled my Athletics, Blade, and Block skills to 100, will I still be able to advance those skills to 103 later on, or do the +3 bonuses count toward reaching 100? If I remember correctly, whenever I've played Oblivion I've always been careful to reach 100 in Athletics, Blade, and Block before giving the diary to the Gray Prince, although that was just to be on the safe side. But if completing the quest now won't prevent me from leveling Athletics, Blade, and Blocking to 103 later on, then I'd like to go ahead and complete that quest so I can in turn complete the Arena questline.

This is explained on the wiki. You will miss out on the skill increases, which will affect efficient levelling.

Yeah, I read the Wiki page carefully and decided it was best to wait until I've gotten those skills to 100 naturally. I'd been hoping to wrap up the Arena questline, but oh, well.

I'm close to finishing the Thieves Guild questline; I've just been given the job of stealing the Elder Scroll. I've held off from working on the Mages Guild, Fighters Guild, and Dark Brotherhood questlines; I got recommendations from the Bruma and Cheydinhal Mages Guilds before deciding I wanted to take things one guild at a time, and I joined the Fighters Guild in Cheydinhal and accepted the first job, but haven't delivered the weapons yet.

I figure I'll do the Dark Brotherhood after the Thieves Guild, then the Fighters Guild, then the Mages Guild, then the main questline. After that I'll do the Knights of the Nine, followed by the Daedric quests and the Shivering Isles. At least, that's the plan.

My thinking is that I've started out on the wrong side of the law but am gradually becoming a respectable citizen. In fact, now that I think about it, it might make more sense to do the Daedric quests and Shivering Isles after the Dark Brotherhood and before the Fighters Guild.

Somewhere in all of that, I'll wrap up the Arena questline as soon as I get the affected skills to 100. And I'll do the other training quests whenever it's safe to do so.

I haven't decided when to work on my Enchanting skills. I've already become a Master of Alchemy, although so far I use Alchemy strictly as a way of making money by selling my potions and poisons. I've never made much use of potions to help me in the game, and I've never made my own enchanted gear. I was thinking that after I've done everything else I'll start a detailed study of Alchemy-- i.e., combining four ingredients to make special potions and poisons that have useful combinations of effects-- as well as making my own enchanted gear. And in the final stages of my end game I'll work on decorating my houses just so, stocking up their larders, accumulating personal libraries, and filling my closets with every type of clothing and armor available.

If you do the last few fighter's guild quests after level 22 you can get a lot of magic deadric and glass gear off the Blackmarsh guys.

Thanks for the tip. I think I'm already over level 22, so I should be able to get that gear.

I finally got to 100% Blade, Block, and Athletics-- Blade long ago, Block much more recently, and Athletics just the other night-- so I was finally able to finish the Gray Prince quest and get the +3 reward on those three skills, kill the Gray Prince to become Grand Champion, and get invited to join the Dark Brotherhood.

But now I'm wondering-- do those +3 additions count toward improving their respective attributes? The only one that still matters is Speed. So far I've got Acrobatics up 3 (from 97 to 100), plus Athletics up 3 (also from 97 to 100), so that's 6 points towards improving my Speed at next level-up. Does the +3 bonus from the Gray Prince's training make that 9 points toward improving my Speed? Do I need to improve Light Armor by 4 more points, or just by 1 more point, to get 10 points toward improving my Speed at next level-up?

No. It's supposed to be a Fortify Skill effect, which does not count towards either levelling up progress or attribute bonuses.

https://en.uesp.net/wiki/Oblivion:Free_Skill_Boosts#Abilities

Ah, okay, thank you! I did read that section a while back, but I wasn't sure. So I'll have to increase Light Armor by 4, which also means I'll need to stop working on Blunt increases since I need only 4 more increases to level up and Light Armor is one of my major skills. Now comes the fun part of switching from Heavy Armor-- which is at 100% and I've got a full suit of enchanted Daedric armor-- to the best pieces of Light Armor that I have. It's kind of nice that this also coincides with having joined the Dark Brotherhood and using the Shrouded Armor and Shrouded Hood while I'm doing contracts.