SX50 has good reviews. It looks SLR-sized. Mega zoom looks like fun for a beginner.
John would just have to give a bit more info on what kinds of photos he wants to take - if he has taken photo classes before and currently owns an SLR, and said he would like to dabble with lenses as he gains experience, any SLR from a beginner model to a $5000+ pro body will have full auto modes to make them behave like a point and shoot, should he wish to default to that.
But you won't really learn why your pictures are not coming out like you want until you start to control the camera instead of it making all the decisions. Generally, the more point 'n shooty it is, the harder it is to access the basics like he has on his current camera. You can do it, but you have to dig through menus and read, read, read those manuals.
John, you said the equipment is "vastly different", but actually pro digital cameras are very much like film slr's of old. Just dreamier
The basics of exposure, shutter speed, aperture, focal length, composition haven't changed a whit.
Bet you could get this for not much over $100
http://lasvegas.craigslist.org/pho/3919323416.html
Someone mentioned Sony Cybershots - if you want an absolutely killer bargain, look for some old versions of those - many of them use Zeiss glass, often considered the best in the world. And have great macro capabilities. This was with a 10+ year old Cybershot 5mp camera, you could probably score one for under $100. Hope this works, haven't tried to post an image yet: