Hmmm, ok first, depending on the size of your laptop (obviously), I’m thinking the single flap maxi is your only hope if you want to try to fit your laptop. Of the three listed, the jumbo is the smallest bag, then the 227, then the maxi. And the difference in what you can carry in a single flap versus a double flap is significant. The double flap takes up a lot of space (but provides a lot of structure, so if that is important to you, that is definitely something to consider).
Second, you might want to think about the length of the drop. The strap on the jumbo is a quite a bit longer than that for the 227 and the maxi (so despite the size difference, the weight of a SF jumbo vs a SF maxi is surprisingly similar because of the difference in the length, and thus the weight, of the chain). If you want to carry the bag crossbody, the jumbo is probably your only option.
Third, as mentioned above, you might want to think about weight. The double flap maxi will be the heaviest of the bunch and might get heavy after a while.
Fourth, durability…if you are like me this would be a real consideration since my daily work bag really takes a beating. The reissue will probably hold up the best - assuming you’re looking at an aged calfskin 227, that is a very hearty leather, plus the nature of the leather tends to hide flaws beautifully. On the other hand, in all likelihood the jumbo lambskin will show a multitude of scratches in pretty short order if used as a work bag. I’ve had great success with buffing out almost every scratch on my lambskin bags, but none of my lambskin bags take the kind of abuse I deliver to my work bag, so keeping a lambskin work bag looking new-ish might be a real chore, if not impossible. I’m not sure which leather you would select for the maxi, but obviously caviar would hold up much better than lambskin - the maxi is so big it’s hard not to bang it into things, so the lambskin, in particular, would show a lot of dings.
Lastly, style. The difference between a CF and a reissue is pretty significant. Some people don’t want the double c’s so visible on the bag they carry to the office (and some people do) - it’s very personal. The reissue is more understated. The CF screams “Chanel” and is a bit more formal (again, the leather plays a role in that too). It all depends on your style and what works for you.
Those are the major considerations that popped into the top of my head when I first read your post, but I’m sure there are others. Good luck making your decision…what a fun decision to get to make! Enjoy!
