I am recovering from a long neurological illness. I work part-time, my wife works full-time, we live frugally. Cycling has done a lot for me and my wife sees the value of a cross country trip. We are planning the trip for 2014. I imagine at that time I will have increased my freelance clientele quite a bit and may be working close to full time but with planning I'll be able to make time for the trip.
As far as finances, there are little things you can do that over time will make a huge difference. We downgraded our cable/phone package and are saving about $90 per month, we also grocery shop every 7 instead of every 5 days, we have dumb phones instead of smart phones, and we don't spend money on little things that don't make our lives better or bring us joy. Surprisingly we haven't missed any of the above and it all adds up to 3-4k per year, which will pay for an entire cross country tour.
If you need gear, planning a couple of years in advance gives you the luxury of watching for sales, which can amount to hundreds of dollars in savings. There are downsides to this of course but REI has credit card offers that includes a $100 gift card. If you are near an REI or know someone near one you can go to their scratch and dent sales. Grocery shopping with an Amazon credit earns reward points to buy gear (about $100-200 per year).. Also, you can obviously save money on the type of tour that you do... Originally I thought credit card touring was for me but now I think that camping and generally keeping expenses down is the way I prefer to do it. I'll probably do a hotel every week or two but to me it seems purer, more of an adventure to stay close to the land and do it all on the cheap...