Good feedback guys.
I'll go more in depth and help answer my own question.
TLDR - Daimyo's are by far the faster choice for both unlocking your first idea set AND attacking Ainu and/or colonizing northeast of Japan towards the tribes there so you can jump over to Alaska.
Tech/Ideas:
First off, most Daimyos are 3/3/3+ or better. Uesugi's ruler, in fact, starts at 4/4/4. This ruler might have the best starting stats. Conversely Ashikaga starts at something like 1/1/4. Considering a total of 9 points is "average" the Shogunate ruler is pretty abysmal and you'll fall behind on Admin and Diplo tech early as Ashikaga.
Playing your cards right by prioritizing admin tech over cores and you can unlock Admin Tech 5 sometime in the mid to late 1450's. You can't colonize anything northward yet because you can't reach anything, but you've unlocked your first set of ideas already and you've spent less admin points due to Renaissance tech penalty than if you waited. Those extra Admin points can then be used to help develop your port to help spawn Renaissance later.
Uniting Japan as Daimyo/Taking Ainu as Ashikaga:
It's roughly 1460 and I own the Northern half of Japan as Uesugi. Your result may very and power gamers might be able to cut this time in half. I predict, based on how I've set up my alliances and enemies, I'll own all of Japan by the late 1460's, if not, I'll have everything for sure by 1470. I should then have 30 years to attach the Northern tribes and colonize towards Alaska.
As Ashikaga, you can annex daimyos and you might be able to annex Nanbu or Ando, but there's two kickers that could royally screw that up.
#1 You can't annex ANYONE for 10 years. So you can't even start to annex daimyos until November 1454.
#2 Shiba sits right next to both Ando and Nanbu. There's a very good chance the AI Shiba or AI Uesugi will gobble those provinces up.
Then you add to the fact that anyone that takes those most northern daimyos is then bigger means they will take longer to annex and this option quickly starts looking pretty unlikely.
So you add the monarch point deficieny and the issues with Annexing, and Ashikaga just isn't an appetizing option. Then you remember that Ashikiaga has pretty piss poor ideas like TenshiN mentioned above and you give up on that Shogunate entirely.
Daimyos are the fastest way to unite Japan and are more or less even when it comes to colonizing efforts. Daimyos will unlock the tech/ideas faster while Ashikaga might be able to grab the actual tribal land faster.