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Well, after each one we have said never again. Though have then ended up doing another one 5 years later. Still swearing about the cowboys who did the last one - so it might be a while before another.
Quick recap of Grand Designs will show you everything that can go wrong but the pain is in the managing of the process - it becomes all-consuming.
Likely things to go wrong - unexpected costs; delays to availability of things (eg windows) or trades; something will be done wrong and have to be re-done; you will have to rush decisions on fittings you forgot to think about beforehand (switches, sockets, door handles, cabling); bad weather; building regs stops you from having something/makes you have something grim even though every house on TV seems to has got round it; it over-runs and you are sharing one bedroom with your 3 teenagers and a dog on camp beds and one shower between you; cost of skips, scaffolding and the aforementioned VAT onto everything.Hit me up if you have any specific questions.
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it won't kill you but the tedium of having to make lots and lots of decisions about things you might not necessarily care about (when pitched against your wider vision) could put you into a stultifying torpor. especially when you've not unlocked the infinite money cheat and so you're making choices which will either have compromises or necessitate compromises elsewhere. you need to figure out the hard line on where/what you will compromise. there will be things you just don't care about either, but which are super important, and so you kinda need to learn to care
we'd just finished our place before lock-down thankfully (bought aug-18, process kicked off shortly thereafter, completed feb-20) - it's great now but, god, those 18 months were a slog
Having done loads of conversions/extensions, IMO in your position you are better off buying 'done'. If you don't have a vision of what you want the whole process will be horrible - it's tiring, stressful, long, expensive and messy.
It's really worthwhile doing if you know what you want, but the process is still hard work.
Buy a place you really like as it is.