P.S Is it better to go on a guided trip first to learn the ropes?
I doubt it: guides are a sensible option for things outside your experience where technicalities like rope work or skiing smarts can make the difference between a great time and death, but going for a walk with a camp really isn't that serious. The only difference between what you propose and what you're already doing is carrying a bit more and stopping overnight. Start in summer when good weather is forecast and you should be fine, plus an added buzz of doing it yourself.
With a budget of a grand you're spoiled for choice. You may well want a bigger (but not enormously bigger) pack, but again with your budget that's not a big issue.
I'd suggest something to cook with, or at least make a hot brew, and as well as a sleeping bag a good mat will make life much more comfortable.
Here's one possible breakdown of how I might spend that money to do what you're after. I've not shopped around for the best prices and this is just one set of many possibilities.
Alpkit Pipedream 600 sleeping bag £170
Alpkit Airo mat £40
MSR Hubba HP solo tent ~ £300
Primus Gravity EF stove ~ £60
Lightwave Fastpack rucksac k~ £100
On top of that you'll need various sundries like pots and pans, gas for the stove, but that gets you some very reasonable kit and leaves plenty of change.
For a rucksack it's very important you try them on with a representative load inside. Different folk come in different shapes and what works for one person may be torture on another. Similarly, if you can have a crawl around a few tents that's time and effort well spent, as on cold and rainy nights you'll be spending a lot of time looking at the inside...
The sleeping bag suggested there should do pretty much all year, but you can get away with lighter in the summer. Lighter means less to carry, and less to pay too.
For your first trip, make it the garden (or a pal's if you don't have one). Sounds pathetic but it means you can get familiar with layout, pitching and what does and doesn't work right next to an easy bail out.
I don't think there's any point doing "guided" trips, although a two-day walk with some kind OM member from your neck of the woods would amount to the same thing and might give you some useful tips. Generally though just get out and give it a go -- in most parts of Engalnd it's easy enough to pike out if things go wrong.
As for what tent, I like the Laser Comp a lot. Very light, easy enough to put up, has stood up to some nasty weather and is actually pretty roomy for me, and I'm over 6ft tall. But there's a few other decent lightweight tents around, and most folk will recommend the one they use -- suppose this shows there are many that'll do the job.
Difficult to recommend a sleeping bag without knowing how hot you sleep, but I'd look at some of the offering from PHD and determine what would suit you. I like the TAR NeoAir mats myself, but there are plenty of other good options, including the Alpkit ones at a much more reasonable price point.
I'd go for a canister mounted gas stove, simply for ease of use and relatively low weight. Meths are generally lighter, but might be a bit daunting for a beginner, while multi-fuel are overkill for the UK, I reckon. Something like the Optimus Crux maybe.
Then see if this, your other cooking gear, clothes and food will fit in a 30l pack. Some folk manage it, but not me. You migh have to get one at 40l, perhaps.
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