All seems like overkill to me.
Send the flight plan the night before.
Get in your plane and go.
If you want to fly high do so - I like to be at around 8,500 when going up north - good to know that instead of being 150 miles from land that I can glide and only have to swim 135
Always fascinated by the tales of daring do crossing the channel - not a flying challenge more one of dealing with the paperwork.
Here my international flights (bear in mind I have to register a local flight plan just to fly in the circuit), is weather (either brillian or hurricane!), a flight plan, eAPIS, Ayscuda, half a dozen gendecs - take the gendecs to the customs with the Ayscuda - first time was a nightmare - now it does smoothly - the flying a hundred miles from land is not an issue - when anyone comes here and rents my airplane they seem very intimidated by the paperwork, but do it once and it's easy - the flying part is always the easy bit; going with someone else doing the paperwork the first time is proably best.
Oddly on the way back it seems weather and a flight plan s the order of the day - try to do the eAPRIS if I can get access, usually can't, no need for an Ayscuda (think it is a commercial thing, but here they have us all get one)
It seems fearless private flying long distances in light airplanes is a thing of the past - was reading an article a few months back people with biplanes in the early 1930's flying to Poland for a picnic.