I think about the things I bought when I started, and my reason for buying them, then look at how many of them turned out to be winners and are still with me. The number was small!
I bought a Basha type tarp. - used it but never had to live under it in rain. Small. It was horrible material and hasn't seen the light of day in years. Tarps are great, but buying one without having seen and handled any examples is asking for trouble. Better reviewed kit does reduce the risk. Bought the Basha before the recent explosion of quality tarps.
I got a Zebra billy can, which was great on a fire when I didn't care about weight, and a pain on a stove when I was trying to reduce pack weight. sold
Snugpak Softie Code Green No6 sleeping bag. Wasn't bad, not all that warm except in summer and retired in favour of a down quilt, but not a bad item.
Snugpak Rocket Pack back pack. Horrible. Bought it because it looked like a cheaper Sabre 45, which was what Ray Mears used on TV. The Snugpak back was so short in its back that it killed me every time I carried it, and I am 5'8" 155lb, so don't need a special fit. Sold
Snugpak Bivi. Bought from SASS Kit because their bivi was recommended to me, not advertised as Snugpak. Could fit me and my No6 bag in, fairly snugly. Could not fit a pad in, could not fit the Softie 10 I got for winter. Sold it after advertising for some one very thin! Made my own bivi that can swallow pad+winter bag+a quilt and still have room to move!
Thermarest Classic 3/4 length pad. Heavy, and required me to hitch my feet up on my pack or something else to avoid lower pack pain and cold feet. The Classic was thicker than standard, and bulkier. I knew nothing about the subject and simply went on a recommendation in some book and ordered the first Thermarest I saw! Since replaced with a full length first gen NeoAir and a full length RidgeRest.
Early winners were a Gransfors Small Forest Axe. Ordered from Woodlore without knowing anything about what alternatives there might be and never regretted it! Paramo Alta rain coat, too warm for summer use, but turned out to be a great coat through the colder months. Still using it about 12 years on. Meindl boots Still in use after 13 years.
If I had it to do again what would be different? That's hard. Times have changed, what is available has changed, prices have changed, the internet has expanded and opened up access and reviews to way more gear. I also know what kind of trip I enjoy and am likely to go on, so spending more on titanium cook pots, sil-nylon tarps, down quilts and super light sleeping pads is more easily justified. If I had spent on the top gear to start with I might have saved a bit in the long run. Writing it down like this, I do see a bit of a pattern, the stuff I bought because I was trying to save money has mostly been retired after not altogether happy times, and the stuff that I bought because I wanted the best is still in use and I have been pretty happy with. Still, I am sure that if I had tried to by the best of everything I would still have made bad some choices and had very expensive gear to upgrade, rather than just mediumly expensive!
If you are interested in hammocks, I can recommend Matt at UKHammocks. After many years with a Hennessey Exped Asym which I was pretty happy with, I got a WoodsmanX and really like it a lot!