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Honestly I would wait till the weather is nicer and buy a mid range back packing tent. Is it possible to do what you want to do with what you have yes, but if you haven't practiced what you setting up camp in the dark or in a little rain, you are likely going to have a really bad time and give up and not never want to do it again.
Meh, I call it a "steep learning-curve" 😉
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Yes learning from failure is important but I would recommend not running into a brick wall, you want to identify small things to do better next time not have a catastrophic failure and not know where you went wrong.
Also exposure is no joke, last thing your want is SAR pulling you out.
If you are set on using a bivy practice settings it up before you go out, even if you live in an apartment just set it up a few times, try it with the lights off and using a head lap.
As for keeping the rest of your gear dry is this tricky with a bivy and best way is to get your kit refined down to some that will fit into your hood when you are sleeping.
As for tarps I would bring two, start with setting one as a little shelter with trekking poles and rope, set the other as a ground sheet after that. Then you have a kinda dry area to work with.
But again doing all that in the rain in winter is very very hard, and I would recommend trying it in the spring/summer and build the skills.
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Hmm, I get where you're going for. I'll start my adventures near home, worst case I'd simply pack-up and move back. 😄
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Other recommendations, learning in a vacuum is not the way to go. if you know someone who already goes camping/backpacking , get them to go with ya, they will be a wealth of knowledge. Even if you only have someone interested in getting into it as well have another person around great for learning and a whole lot safer.
If you don't have them, dry bags, I don't mean a waterproof ruck, smaller dry bags are the way to go. I have a couple outdoor research one, the heavy duty ones are great for tents and stuff, compressible ones are great for clothes.
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Yeah I'd love to go with someone else, I simply don't know or find anyone who wants to...
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See if you have in clubs or stuff like in your area, of you got an outdoor store near by they might be a good place to start. That or who knows maybe another outdoors bitcoiner on here lives not to far away.
Form the bivy you got I'm guessing you are in the UK and already know this but for the love of God no cotton, stick to wool and synthetic clothes.
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Netherlands 😄, yeah I've got my Woolpower clothes ready-to-go.