Urahara Versus Jyriya
Writer: This is something that I thought up whilst ranting to myself. Now while I may know a Jutsu or two, I know more about Urahara. What it comes down to is which one would last longer in sustained combat. So I have brought in Yoruichi to discuss Urahara's strengths and weaknesses
Yoruichi: Thank you writer
Yoruichi: Ninja (generally) choose to forgo extreme strength in exchange for more stealth abilities. Shinigami (excluding The Onmitsukido) choose to forgo stealth for extreme strength.
But this would be uninteresting without going into the details of each character. So on one side we have the observant scientist who can study how one might launch an attack. Details he will notice are the focus of energy and the tensing of muscles. Basically, to land a blow you would have to launch an attack without moving in the slightest. However, Justu require hand seals, hand movement to channel energy. You would have to kill him with one Justu but he will know from watching you fight what move you are charging up for use. Even if Jiraiya used a different ability it would take longer still giving Urahara an opening.
On the other hand, Jiraiya could evenly space out his hand seals one before vanishing another after landing and so forth. But this would drain his Chakra reserves greatly making the ability weaker there by ordaining that Urahara would not need to dodge.
Jiraiya then draws Kunai. Let's look at what a tactical error THAT is. Urahara has a SWORD and knows how to use it greatly; he would actually welcome the change to a more weapon based combat.
Remember that Reiatsu functions differently than Chakra. Reiatsu suppresses the area around the Shinigami. Chakra to my understanding needs to be way more concentrated to be used similarly to Reiatsu, but the more Chakra one has the less control one has. Urahara being a captain will be able to muster quite a bit of Reiatsu. Jiraiya's sage mode could be countered by Urahara manifesting his Reiatu.
Yoruichi: Well that is my half of the rant I cannot rant for what I do not know.
Writer: So now, it is your turn Naruto fans. I want to see what you have to say on this matter eventually I will write up the battle sequence and it will be based on a combination of what I have stated here and on what you have to say and I will disregard anything like "He will win because he can." I need reasons that you think your representation might win and who will be presenting the argument. And if anything said here is incorrect then feel free to tell me how to correct it.