Definitely start with a campsite. Also try and pick a dry night if possible, and for your first attempt a relatively warm one. If you have a back garden you can camp in, that might be even better for testing kit.
If you are away from home, a method of making hot water for tea/coffee is something I like. I'm usually happy to eat cold foods when camping, as long as I can get a hot drink. This also saves washing up over cooking, especially if you are used to doing things like frying bacon as per most camps I did as a scout.
Another tip I'd give is that roll mats and self inflating mats may be tiny and cheap, but unless the ground is soft you may not enjoy sleeping on them. I was always happy with them when I was younger, but I use a syn-mat now (if I ever get round to camping - it's been a while
). Cheaper and at least as good if you are car camping would be a blow up airbed.
With poles, I've found that alloy poles are far easier to put up than fibreglass ones, as they form a smooth pole when fitted together. The annoying bit of feeding a fibreglass pole through a tent tends to be the metal connectors snagging on the material IME. On the plus side, fibreglass poles are easier to repair if the campsite dog decides to jump on your tent and smash them. Alloy poles take a bit of inginuity to keep going