I'll throw some info your way. I have been involved in photography since 1981, 3rd grade. I have always used Canon cameras so that is what I know and prefer.
Evaluate what it is you and your significant other are primarily going to use a camera for. Think about if a DSLR will be a grab and go camera. Will you really be willing to haul the gear? Most entry level DSLR's aren't too bulky and entry level lenses work really well but it puts off people from bringing the camera with them. The newer DSLR's also feature great video capability.
There are point and shoots out there that work very well for most things. It is not pocketable really but the case I put it in can be shouldered, holds a spare battery, memory card, and even a small tripod.
I have both a DSLR and a high-end point and shoot. I try to take the pns with me all the time and the DSLR when I have a specific interest in mind. If you go on a lot of trips an underwater case may be a good idea to invest in as well. After I purchased my first digital, which was a Canon S45, I then picked up an underwater case. When I went to Hawaii a few years ago it was so cool to take underwater pics while snorkleing (sp).
My current line up is a Canon 5D with two L lenses and a Canon G9. Both are a couple years old and have been replaced with other models. If you do decide to make a purchase keep in mind Amazon (no tax and free shipping) or B and H Photo (no tax unless you are in NY).
This is a great site for Canon enthusiasts and can give you a lot of information:
http://photography-on-the.net/forum/index.php
They have a great transportion section where some incredible aviation photography can be found.
Photography is not what it use to be and can be learned fairly quickly. What takes time to develop is an eye for scenes or set ups which may ellude the layman.