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Spending £50-100+
I think unless you're getting a deal (seconds, 2nd hand, etc.) £100 isn't a great price point. £75 and below seems to give you better value with shoes. £150 seems to be the start of taking you into decent shoes.
Red Wings do seem to be very "now" so while they may last a lifetime, I guess whether you will be wearing them in 5 years time is the question.
But overall I think you're right. A quick Google says they're c£250 so if you spend between £50 and £150 odds are you're probably paying a premium for little quality gain. Over £150 and I guess you may as well cough up the extra dough for what you really want.
Tl;Dr £35-50 on Asos clones, or buy the real thing. Maybe.
Do it, highly doubt you'll regret it.
Spending £50-100+ on a pair of boots then thinking maybe you should've got the Red Wings instead though, that'd sting.