Mid-Life Crisis Travelling

In the last few weeks, I’ve had the full range of responses to our decision to give up work and travel. These generally seem to boil down to metaphors relating to bravery, living the dream, and prison break from fellow inmates. I'm starting to feel like a cross between George and Lenny and Papillon. After all, I haven’t escaped yet, not until December and am desperate not to tempt fate.
I’m still busy tunnelling away at Tom, Dick and Harry. We’ve booked the plane tickets from Manchester to Myanmar (Burma) in January and we’re planning our first few weeks in this amazing but troubled country. Even now, you still can only go to certain tourist areas.
Myanmar has given us our first travel dilemma. After a few days in Yangon (Rangoon), the travel options for our next stop in Bagan are:

12 hour bus journey arriving at 4am £30

17 hour train trip £40

1 hour flight £80

Which one would you plump for?... I’m totally ashamed to say that we’ve chickened out of the chicken bus and have booked the flight. I hope that I don’t regret this decision having just read Myanmar's airline safety record.
But it’s made me think about how we’re going to cope with the day to day crustiness of long term travelling? Will our trip end up depressingly as a world tour of Novotels? Will we get to meet and spend time with the local people? Will we share dorms with the twenty-something GAP year hipsters? Will we publicly humiliated and banned from hostels for being too old?
Then there’s the new reality of carrying 3 months of Gafyn’s heart meds with us. Apart from getting them into the 40-litre backpack and through customs, word online is that you can only get two months worth of pills off the NHS. We’re going to have to start squirrelling and stashing them now to last the trip or we’ll wind up in the full moon beach party trying to score cholesterol busters.
I’m sure I’m not the only ‘mid-life crisis’ out there who’s given up work to go travelling. I’d be really interested in your experiences: the good, the bad and the ugly.