Not sure what you mean by date ranges?
What I would do is use the netbook to run PQs each evening, or maybe once every couple of days, for the areas you're visiting, and download them into GSAK, then stick them on the Oregon as needed.
You could do it before leaving home but if you do the whole of the UK then I suspect you'd be getting a vast volume of data for caches you wouldn't be going anywhere near - and by the end of the holiday it would all be 3 weeks out of date and you could waste time going for caches that have been disabled, archived or had co-ords changed.
GAGB Member since 2009
UK Mega West Mids Committee - Treasurer 2011 - 2013
GAGB Committee - Treasurer 2016 -