I'm level 58 currently and aside from today i have been getting 400 gw gems with difficulty a day my team is
5 star sid
5 chewy
4 fives
4jawa
4jc
4poe
4Talia
4phasma
Rotated depends on opponent. Now, I know I'm short on healers but should I cease levelling and finishing daily activities to strengthen with gear/shards? Btw, my opponents are level 60+ monsters with 7 stars on nearly all characters after I get about halfway through.
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Apart from the above, you seem to have rushed to 58. You'll need healers, all you can get, to consistently clear GW. So farm them and I would hold up training Chewy etc until you really need to for clearing campaigns and such.
Build a roster 1st, then work on gearing them up past 4. It's gonna be a grind either way, but if you have a roster of different toons, you'd at least have some choices in your squad compositions. The alternative would be a few powerful toons which you wouldn't want to use when you're higher.
But yeah, in GW, healers are my problem I think. I did well today because I didn't come up against dooku(for once) the damage kills me I usually win the first difficult battle but with low hp as they seem to target my healers.
I suggest you don't invest too much on the 4, though JC comes in handy for GW. At higher levels, he's quite good.
Consistency is my biggest issue with this game.
I run:
Phasma (leader)
1st-O TIE-Pilot
Kylo Ren
Luminara
Daka
as first team, with Jedi Consular as healing-backup and Sidious as dmg-backup (and plenty more if the need really arises).