Imho, Kael gear isn't a *huge* upgrade to the chaotic gear you obtained much earlier, but since you've already done it, many kudos to you

I'd also not bother with upgrading those kael armor pieces with the quested armor versions in SH, the upgrades are lackluster at *best*. Focus on getting the normal drops from SH/etc, which are a huge upgrade to the stuff you found in sebilis/etc. Also, if you don't have it already, focus your PP on purchasing *all* your t8 spells from bazaar. They are pretty cheap (minus the ones purchased via points, which usually run 10-40k like the mage/nec pets) and make a huge difference in DPS/survivability.
Also, for flags, you may want to do an /auction that you're seeking a number of vulak tokens if you are drastically low on PP. Most people just slaughter vulak every day as a side thing when they run into ToV to farm Lady M for her coth orb. You may be able to find these tokens from a generous player for cheap simply because they don't want to keep them on their bazaar mule forever (most people farm up plat to buy the t5 token and ignore the lower vulak/sleeper tokens just to avoid the hassle of doing more flagging, so the vulak tokens don't typically sell very well.)
Once in ToV, work on your armor quests there. Some of the clickies from those pieces are used to darn near end-game, and are supremely helpful (bp/legs primarily.) It'll be tough going at first, but this is a game and at least to me, the tougher something is the more fun the event

You could go the easy route and get flagged for stillmoon, where the armor drops off trash mobs and is equal in stats, but those pieces lack the clickies.
All in all, platinum is your main objective at this stage in order to make breaking into t2-3 much easier since you're only going in with 6 toons (I'm assuming no donors?).
Edit: Also save up ALL those radiant crystals. The armor/augs you can purchase with those things are unbelievably amazing. When auged, they're better than anything you'll find t5-ish, maybe higher. Some players sell their crystals (unsure of what they sell for) whereas other more established players merely give them away as they really serve them no purpose anymore

Best of luck to you!