I'm not sure I would suggest changing your footstrike while at 100 miles. However, since outdoor's is ending, now is the time to do it. Like all aspects of running, you should never add too much of a stimulus or multiple stimuli over an alotted period of time, i.e. less workouts while building mileage or anything similar to that. Everyone here will say this, but the key really is to build up gradually. Your calves and achilles will be working much more than usual, so you don't want to overload them. Personally, when i changed footstrike, i jumped too quickly in the middle of my changing period, and thus strained my achilles. I would suggest doing it similarly to building a base, and tracking miles ran with a different footstrike, using the 10% rule and 2 week hard 1 week easy rule in conjunction with how many miles you ran forefoot/midfoot or as a percentage of total weekly mileage.
As far as wearing lighter shoes, it could help, but it also isn't a mandatory type of thing. The key with minimal shoes or barefoot is that there is less of a difference in heel to toe drop, as well as less cushioning, so that your form will adapt so as to avoid injury. I personally feel that this is taking a larger risk than necessary, so when i changed i wore my regular trainers for everything except workouts. The key in wearing regular trainers is to find the feel of running differently, then slowly incorporating that into your stride in multiple phases. A good way to start would be to see how it feels to forefoot/midfoot strike. I've found a good way to do this is by standing on your toes, then jogging in place, making sure your toes touch the ground first. Once you start that, you can slowly jog forwards, again making sure you land on forefoot. Personally, once i got used to the feeling of landing lightly on my toes/midfoot, rather than trying to switch to that in the middle of a run and stomping down on the ground, the change became much easier. After changing the footstrike i similarly have been trying to bring my foot more under my center of gravity, and finally i have worked on more active hip extension while running. Hope the change goes well!