Okay. Here are my thoughts, running down the list:
x] - Fuinjutsu:
[x] - Reverse-engineering the controllable, detonable shuriken.
[x] - Try to create a basic chakra storage seal.
The control and explosions of the shuriken imply progress on learning how to create anchors for chakra strings, and explosive tags, both of which will be useful. 7/10.
Chakra storage seal. If it works, it's fantastic.
If it works. However, even on a failure, we'll likely gain additional fuinjutsu experience, and additional chakra knowledge (chakra transfusions, perhaps.) 8/10.
[x] - Ninjutsu
[x] - Learn the Shadow Clone jutsu, then teach it to Naruto.
[x] - Pay for a mission to retrieve a summoning scroll from an Uchiha weapons depot and sign it. The others will be retrieved but not signed.
[x] - Cat
[x] - Hawk
[x] - Raven
[x] - Crow
If we have the chakra for them, then summons are an incredible force multiplier - not just in combat, but also in training. I'd shy away from the crow contract, given Itachi's whole deal, but any of the other three are promising.
Hawk, in particular, provides aerial surveillance even at a low level, and later on probably has decent Wind jutsu to go with it's flight capabilities.
It's also a big boost to
Sasuke - unlike the other options, this will immediately improve his level as well. If we're boosting Naruto, we shouldn't neglect our cousin. In addition to being a dick move, it also increases the chance of him brooding his way into a bad end.
Cat Contract: 8/10
Raven Contract: 8/10
Hawk Contract: 9/10
By way of comparison, the Shadow Clone Jutsu... is probably a trap. We can't use it ourselves for years, yet, and teaching it to Naruto will raise questions we'd prefer not to have asked. This is something we can ask Naruto's teacher about (or tell
him to ask about, if we get different teachers) once training proper begins. 3/10.
[x] - Genjutsu
[x] - Learn more Sharingan Genjutsu
Sharingan Genjutsu is the cream of the crop, especially since its hand-free nature combines well with swordplay. 8/10.
[x] - Kenjutsu
[x] - Learn techniques intended to counter ninja from a former Samurai.
[x] - Try to integrate your Wind Release with your kenjutsu
Both of these are autopicks for me. Getting gud is important, we're
going to be facing ninja, and Wind Release as applied to blades is pretty fantastic - see Asuma. 10/10 for both.
[x] - Iryojutsu
[x] - Investigate dojutsu specific techniques.
[x] - Learn the Chakra Scalpel
These, on the other hand... "Dojutsu specific techniques" basically means eye transplants, as far as I can tell. And while those will probably become relevant eventually, I'm unconvinced that they're worth a precious training slot now, of all times. 4/10.
Chakra Scalpel is similar, really. We aren't going to get on Kabuto's level with it... well, ever, really. We don't have Sakura's talent for chakra control, and the time it would take to get the chakra scalpel technique up to the level it can be applied to our swordplay would almost certainly be better spent on other pursuits. 2/10.
Going through the list, my top six actions individually are:
[x] Plan: Be Prepared!
[x] - Kenjutsu
[x] - Learn techniques intended to counter ninja from a former Samurai.
[x] - Try to integrate your Wind Release with your kenjutsu.
[x] - Pay for a mission to retrieve a summoning scroll from an Uchiha weapons depot and sign it. The others will be retrieved but not signed.
[x] - Hawk
[x] - Genjutsu
[x] - Learn more Sharingan Genjutsu
[x] - Fuinjutsu:
[x] - Reverse-engineering the controllable, detonable shuriken.
[x] - Try to create a basic chakra storage seal.
Doubling up on fuinjutsu probably maximizes the chances of getting chakra storage going. Additionally, being able to create our own explosive tags means we'll have a ready stock once the fun begins. Having chakra storage lets us get more use out of summons. Hawk summons in particular go well with our Wind Affinity, which we're applying to our swordplay. In addition, we'll also be able to apply hands-free genjutsu in the middle of a sword fight, and we'll have the techniques ready if we need to face ninja.