At the risk of stirring the pot...AND...acknowledging favorable bias toward the gear that I own, I followed a very different path as a beginner. In the best spirit of gear geekdom, I spent a LOT of time doing internet research, reading forums and looking at gear in stores (even talking to salespeople when I had to). IMO, there's a lot of "wisdom" from the experience of other users, especially on this forum.
I'm also old enough (!) so that I've been through the buy-cheap-to-start-and-replace-it later-once-you-know-what-you're-doing mind set more than once. My hindsight suggests that doing research and asking questions and then stepping up to buy gear that is well-regarded from retailers/manufacturers with reasonable return privileges is ultimately cheaper than trying out on the cheap and then upgrading. YMMV. If I find I really don't like what I bought when I try it out and can't return it, then there's usually a ready market for selling the nearly new good stuff to other enthusiasts for a small discount.
For my entry into hammock usage and leaving my ground-dwelling habits, I bought a Warbonnet Blackbird and an OES MacCat Deluxe as my initial purchases. I couldn't be happier with both choices. Good products from good people!! I'm not replacing anything from my initial purchases. Quite the opposite since I also added a 3 season Yeti UQ and a JRB MW4 UQ to extend into the cold Minnesota winter, with a BBO top cover from Paul Gibson and Winter Dream tarp from Scott Littlefield on order.
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