That @tjwaugh , is a question that tends to elude all of us!  Whether you have years and miles under your boots, or are just starting out, such as yourself.

First and foremost, figure out exactly what you want to accomplish and what your priorities are.  For example, if you are more of a camper, who hikes to your destination but wants some creature comforts, then you would probably forgo the ultra lightweight gear.  But, if you intend to put miles behind you and the camping part is just a slight delay on your distance goal, then you are a likely candidate for ULW gear.

After that, focus on your shoes (and socks), your pack, shelter and sleep system.  You'll want to try on the shoes and pack as fit is hugely important with those items.  Read everything you can.  This Conversation page and the Co-op Journal are great places to start.  Talk to other backpackers and hikers that you know.  Ask the folks at your local REI store, both employees and customers.  

After that, if you stay in this hobby/lifestyle for very long, you, just like Goldilocks, will be embarking upon a lifelong search for items that are "just right".  And as soon as you find that something, a new, fancier/lighter/stronger/etc version will come out.

Enjoy the ride!

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