Hi Andy, I just wanted to say this is brilliant!
I have hired a few people as part of my job and I can tell you that the people who have a much better chance of being hired are those who are motivated, can demonstrate how to move forward or fix problems in times of adversity, and have a zest for life. This trip will give you some great stories to tell in interviews.
I assume you might be able to pick up farm labouring work whilst on the move. If not for money, for food and lodging. If you talk to locals along the way you may fall upon good luck. Warm showers etc is a great idea for improving your chances.
On my last tour in Normandie I met a guy with a dog sleeping in a hedge. He had been on the road for two years just heading south for winter, north for summer. His panniers were plastic bags and to be honest he did look like a bum, but he was happy. Inspiration.
P.