Far more nonsensical than having up to thirty sub actions in a turn that's supposed to cover an entire season, sure. Have fun with that micromanagement nightmare. The point of my solution is that you don't have to spend hours strategizing up to (apparently) thirty posts worth of tactics and maneuvers to either catch up to raiders or, on the flip, raid without being murdered by a vassal's host, not to be realistic, which if you had been paying attention you would have picked up on by now. Also, your contingencies for raiding houses? Do try not to get your head blown off, and keep in mind that anyone whose information on doing anything illegal worth trusting will not be found spouting their immature little finger mouths off on the internet about it. <3
EDIT:
Then again, assuming the hyper in depth raid strategizing doesn't get to be too much for most people to handle, I'm sure it'll make for an interesting read, so from a purely roleplaying/creative writing perspective I do greatly prefer your system as mine is basically just, "sent one hundred spearmen to raid so-and-so's fiefdom. Stole six hundred bullis," where yours requires actual, you know, content. From a roleplayers perspective, however, even if you only write one hundred words per leg of the raid you'll end up writing novels worth of strategy by the time you're fifty seasons into the IC, which sounds, just, dreadful to have to write.