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I often feel the same. Sadly I think that in this country, even when you think the bike/train stuff is sorted there's always a risk that you'll get screwed. You can have a space booked and find that the bike spot is filled with luggage, or on a train without booking you can find that there's 12 other people with bikes who are trying to get on at the same time.
But in the end, these problems tend not to be totally fatal, and any bike trip has a risk of things going wrong, you just have to keep your chin up.
Maybe try plotting some day rides from a station you're thinking of journeying to so you can get the hang of that train before you try and do it on a strict deadline with a week's worth of gear and accomodation pre booked.If you want a single pretty solid suggestion, I found the train to the King Alfreds Way start in Winchester very painless.
Belagerent-
Yeah that one is definitely on my list, I'm in Worthing so I can get to Winchester v easily and as much as the train is full of riders heading off for the SDW its not an issue with Southern carriages.
Initially I was trying to figure out how to get to Frontier 300 (I will probably end up driving to the finish and taking their shuttle, the train is ludicrously expensive and would involve travelling at peak times). I then started trying to plan something for around the Peak/Lakes/Wales etc, and I'm sure there must be good combinations of getting to Manc/Sheffield and then spurring off from there so as to leave London post-peak and arrive at X pre evening rush.
jackbepablo
Something that sort of ties in with what Passhunter was asking earlier as well, is the public transport aspect. I've been trying to figure out some long weekend type solo missions to do this year, and I don't want to drive, but I find the train stuff awkward and I never know which lines are terrible for taking a bike on etc. A pooled resource of what works well from various places would be pretty handy, I think – could just be my own fear of trying something and it being shit though