Midlifeblues: Your main question seemed to be about recumbents. I just got my first recumbent 2 months ago after years of riding upright bikes and I will tell you about my impressions.
First the negatives about recumbents. The biggest negative is price -- my impression from shopping around is that a recumbent cost 2 to 2 1/2 times as much as an upright bike of the same quality. So expect to pay $2000 for a recumbent that is roughly the quality of a $800 - 1000 upright. When you buy accessories for a recumbent you will have fewer choices and often higher prices. The second negative for me is that slow speed maneuvering is more difficult (at anything under 6 MPH, I am noticeably more unsteady on the recumbent.) Starting from a stop is also more difficult which is a problem for me in traffic. I also feel that I am somewhat slower climbing hills on my recumbent.
Among the positives about recumbents for me is that I am convinced I am faster on the flats and really faster down the hills. The slightest, shortest downhill makes my recumbent accelerate to the mid-twenties and a downhill over a hundred yards long puts it in the thirties with little work from me. It also helps with certain physical problems I have had with riding. There is no pressure at all on my hands -- this is wonderful! With an upright bike, I was never able to ride more than a few hours without at least some numbness in my hands. There is also no stiff neck and so far no stiff back on the recumbent.
There are a few things which are sort of a wash between my upright and my recumbent. One is visibility. Recumbents have the advantage of a level head looking straight forward in a very relaxed, natural position without craning the neck -- great for sight-seeing and general comfort; upright bikes have the advantage of a higher seating postion with a better view over the front tire for pavement obstructions, better view over cars in traffic, and an easier look behind. As for rear-end comfort, the recumbent is somewhat more comfortable but there is still a lot of pressure on the hip muscles can cause considerable discomfort.
For touring I would suggest a long-wheel-base (usually abbreviated as LWB) recumbent, meaning that the front wheel is in front of the pedals. On a short-wheel-base (SWB) recumbent, the pedals are in front(and over top) of the front wheel. Easyracers and Rans are both brands that are noted for long-wheel-based recumbents, are respected, and have been around for a long time. Visit their websites. I have also read positive comments about Burley recumbents. There are also websites with information about recumbents that you can find easily using your favorite search engine.
I bought a used Easyracer Goldrush and I am happy with it. I believe it will be superior to my upright for both touring and speed. However, after the first 550 miles I still feel I am learning about the bike. The 1000 miles training some respondents have suggested is probably a good figure to shoot for. Be careful and watch out for injuries as they can stop your preparations dead in the water.
