If his goal is to get recruited, then the only question is whether he's ready to pitch again or not. If he is, then when he's ready he should be at exposure events. If he isn't, then he shouldn't be pitching at all, at any level.
There is absolutely nothing to gain, from a recruiting perspective, from the fall wood bat league in our area. Those games are generally recreational, though frankly they tend to be of such poor quality that it's hard to have any fun at them. There certainly is not going to be any opportunity to get scouted there.
As for Jupiter, bear in mind that exposure can be good or bad. If he's ready, great -- though there would be a need to face some stiff competition prior to Jupiter to be ready for what he'd face there. If he's not ready and he's out there looking terrible while everyone's watching, that can prove to be a mighty expensive mistake.
Jupiter is a powerful event as long as you can perform well on the big stage. But if you create a negative impression, you can get yourself scratched off a lot of lists, too. If he's not healthy, you might want to take the next 6 months to get healthy and then ask the JuCo's to come see him in the spring.
Your interest in JuCo's does help, since they are not quite as accelerated in their recruiting time table as the D-1's are getting. But I would also suggest you not rule out D-2's, who also have money to offer, and who can get you to a 4-year degree in the end without ever having to transfer (or have to sell yourself yet again in 2 years). Don't close any doors in either direction just yet. As with the JuCo's, there are not a lot of D-2 programs in VA, but there are lots nearby that are affordable even for out-of-state guys if you head to, say, SC, NC, WV or PA.