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England for a month/ Britrail pass worth it?

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I'm from the U.S.

I am going to spend a month in England with my significant other who lives in Reading, right outside of London from late december to late-January. I've read a lot of forums on here about the Brit-rail pass and it being worth it or not worth it, but I have a unique situation.

I want to buy the flexi pass which is $385(low season) for 8 days. I will be in Reading for the majority of the 5 weeks I'll be spending with him, but I want to be able to go out and explore every now and then. January being a ridiculously unpredictable month for weather, I don't want to book trips now, and then be snowed out, or have to go to Dover castle when it's miserable (relatively miserable to the rest of January I suppose). So I want to be able to go whenever the weather is at least somewhat agreeable to go see Dover Castle, Canterbury, Warwick Castle, Stratford-upon-avon, Bath,... maybe even a weekend to scotland.

I'm looking at the tickets and from Reading to warwick on, it's £39.00, .. and then from warwick to stratford-upon-avon, it's another £5.20, right then and there, the pass paid for itself on that trip alone (385 divided by 8 is around 50 bucks a day).

I want to make sure I'm looking at this right, or that I'm not missing anything. Would it be better if I just showed up at the last minute or last minute bookings as opposed to buying the britrail pass?

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