using an action surge just to do 2d6 dmg in a turn doesnt seem that great, especially if he only gets 1 action surge per rest, where if he was using a longbow he would get 2d8 every round and 4d8 when using action surge.
By taking crossbow expert and using hand crossbow he can a) make 4 attacks using the crossbow (one normal and one as bonus action using second part of the feat, then another attack because of Extra Attack and theoretically another attack action due to Action Surge) and b) be able to make crossbow attacks at melee without disadvantage.
He can't use the shield either way as both weapons require 2 hands to use, longbow = 2 handed and crossbow's ammunition trait require you have a free-hand to load ammunition (separate trait from "reloading")
Edit: so with crossbow (and feat) he gets 3d6 per turn (4d6 once per rest) vs 2d8 with longbow.
a) He can make 3 attacks with hand x-bow (2 with [Extra] Attack Action and 1 as a Bonus Action) and 5 when using Action Surge. Action Surge gives an additional Action and using Attack Action gives him 2 extra attacks due Extra Attack rule. (PHB 72)
b) Any ranged attack can be made in melee without disadvantage with the Crossbow Expert feat. This even includes spells. Usually every feature has a more general benefit and this is the one on Crossbow Expert. (PHB 165)
While long bow has +1 greater average damage than hand x-bow the extra hit is well more worth it as you also gain your stat bonus with every hit. With a +3 DEX modifier Longbow does 15 (2d8+6) average damage with 2 hits and hand x-bow does 19.5 (3d6+9) with 3 hits.
IMHO the best advantage that the hand x-bow gives is one more attack roll to not miss with. String of bad rolls is what usually gets someone killed and with hand x-bow you get to roll one more time. With Sharpshooter feat the biggest disadvantage of hand x-bow is negated as you don't have to be within 30 feet to be effective. JP really needs to remember to gather bolts after fights as he will be using tons of them.
Oh yes I was getting kinda muddled in the attacks since there's so much interaction between the abilities and feats, thanks for clearing that up! Still stands that crossbow is better than longbow for sure. Seems interesting though, I can't wait to see how this character plays out.
@AdamKoebel Would JP be allowed to load his hand crossbow if he were to have a "buckler" strapped to his offhand forearm? Maybe only have it give +1 AC instead of +2? It seems silly that a hand crossbow is still a 2 handed weapon in terms of the ruleset because of the reloading mechanic.