First of all, how is BJ a better striker then Florian. Saying that is literally like saying boxing is a better striking art then MT. Sure, BJ's boxing is great, but it's only about as good as Kennys MT, so I really don't see him accomplishing much in the standup.
A lot of BJ's fights turn into boxing matches though cos people are so scared to be put on their back that they tend to abandon kicks completely or at least use them sparingly.
On top of that, BJ only has about 2-3 rounds to finish Kenny before he gasses and Kenny brings the apocolypse down on his ass.
When has BJ gassed at 155 lately? Especially when, as you say it's gonna be a mainly standup fight where he's not trying to defend TD's constantly.
Second of all, GSP's camp has BJ identified down to a T. So this can be a very important information for Kenny coming into the fight, especially with Dr. Jackson coming up with an assisting game plan.
But Florain and GSP are completely different fighters TBF. Can you really see Kenflo keeping Penn pressed up against the cage, can you really see him maintaining top position like GSP did? TBH I think Jackson's gameplans are becoming a bit overrated really.
Third, since I've already established in my mind atleast that Kenny's going to win in the standup, if he can stuff BJ from taking him down, it will be a huge part in deciding whether or not he will win. Training with GSP's camp will improve his wrestling by lightyears. And lets not forget how quickly Kenny improves, so this may get his level of TDD to where it needs to be so that he can stop BJ from taking him down.
The problem there is that you think Florian's gonna win the standup due to his superior muay thai and as I pointed out earlier, the kicks leave him open for a TD regardless of how much his TDD improves training with GSP. BJ's got arguably the best top game in all of MMA, outside of Fedor perhaps so if Kenny gets put on his back he's gonna be in trouble IMO.
So overall, this fight comes down to TDD, and training with this camp my be enough to bridge the gap between Kennys TDD and BJ's TDs.
I think this fight comes down to Florians ability to stay on the outside and outpoint BJ, much like he did to Huerta. If Penn starts to gas, then he can pursue a more aggressive approach and maybe even try to put BJ on his back.
BJ's got some seriously underrated TD's IMO, go watch his fight with Gomi, I know it was a while ago but Gomi's got good wrestling and Penn took him down with ease, I think we all agree that by far the most dangerous position for Florian would be with BJ on top of him. TBH I wouldn't be surprised if BJ pushed really hard for a TD early on in this fight and then tried to settle into his boxing later. Penn's looking for a dominant win, and the best way to do that is to put Kenflo on his back early and work from there.
I think the deciding factor in this fight is what BJ Penn shows up. If he comes in motivated I could see Kenny getting outclassed, but if he comes in out of shape then I think we could see him lose and then retire TBH.