Exciting! Sounds like a great way to excercise and socialize! I like to keep my workout gear fairly minimal and on the cheaper end of the spectrum. I find the cheaper gear holds up reasonably well as long as the fit and support was there in the beginning.
General thoughts:
I've never used fanny packs or water bottles, so no suggestions there.
Spend on shoes, save elsewhere. If you don't already have a pair, go to a running shop at let them fit you with a pair appropriate for your gait. Brooks shoes has a decent online quiz that serves a similar purpose. Happy colors are good and make me excited to put on my shoes.
Yes to wicking everything. Find fits that work for you and feel flattering.
I prefer short sleeve v-neck shirts from Reebok (I find them on sale for $10). I have a couple in gray and a couple in other colors. I also prefer leggings or capris over shorts because shorts tend to cause chaffing. Old Navy is my destination of choice for bottoms, but you do have to make sure they are thick enough (some are too sheer). I usually stick to black, gray, and navy so they coordinate with most of my tops.
I like bras with a touch of padding for modesty, but I loathe removable pads. So annoying!
My hair is undercut, so I need a headband to keep things in check. Under Armor makes a great one.
I buy a couple of bags of wicking socks and a handful of thongs from Target.
That's it! The core of my gear capsule is cheap and mix and match. I do have a few outlying tops (tighter, more colorful), but I don't wear them as often. I treat my gear like a uniform. Grab and go.
I'm on my phone now but will link to finds later.