OA5II,
This is just one humble, intelligent, insightful and handsome man's opinion, but I would do it after this season (assuming finances allow).
Some of the factors to look for are: well known organization known for playing a challenging schedule, known for quality coaches, known for quality factilities and reputation. One thing that help my son was that his 14U team played about 40% of its games, especially in the summer, were played on the 60-90 field. That really helped him acclimate quickly when he hit the high school campus.
Also, look for teams that play a good showcase schedule with their 17U and 18U teams, and have a reputation of placing numerous players on college campuses and know the college recruiters.
Most of these types of teams have been mentioned on this site previously, so I won't list them here. If I were to forget one, this post would become chum in a sea full of sharks
.