I guess I'd be considered an advanced hobbyist.  I put my Canon EOS Elan IIe
on the shelf two years ago with purchase of my first digital P&S (Sony W-1),
and have loved the digital experience ever since.  Been saving for jump to
DSLR, and finally bought Canon EOS 5D body yesterday.  I doubt I'll ever
second guess that decision, but can see lots of possibility for buyers
remorse in lens choices.  My only quality carryforward is an EF 85mm f/1.8,
which I know I'll remain happy with.

What kind of shooting do I do?  Almost anything.  I like wide angle scenics
with up-close subjects and/or framing, portraitures with smooth bokeh, long
shots compressing roof tops and hills and whatever, people candids (city,
town, sea shore, at work, at play, you name it), almost any little gem that
yells macro, morning and evening light, long exposures, slow flash with
ambient-lit backgrounds.  Mostly I like natural light (so lens speed is a
priority), and greatly prefer on-location vs. studio.  Sure I've left some
things out, but basically same problem as most of you, my photographic taste
is all over the place.

Personal talent and knowledge?  Well, been told I have a pretty good eye.
I've entered some B&W work in contests over the past 40 years, and even won a
few.  I've done some B&W film darkroom work over that time so learned a lot
about the process.  Already studying digital darkroom (primarily Kelby's
"CS2" and Grey's "Color Confidence") and practicing CS2 on a friend's
computer with generously loaned RAW files, and loving it.  Plan to purchase
CS3 as soon as released.  Finally, I’ve been following this and other forums
religiously to reason through the jump from SLR to DSLR.

All that said, we learn by doing, and till I put my lens dollars on the line
and live for a while with lenses bought (unfortunately for me that means
longer than any normal return period), there's really no way to know how
badly I'll screw-up, the old "buyer's remorse" syndrome.  I know lens choice
is a continuing thing, been there and done that during my film years, and to
some extent there's a guaranteed amount of screw-up (that little pixy on your
shoulder saying "what if").  Just trying here and on other forums to pinch
some minds and maybe soften the inevitable blow.

As a starting point, I'm limiting my selections to Canon (personal taste).
Considering my age (no spring chicken) this will in all likelihood be my last
major photographic tide change, so I'm prepared to indulge myself (already
having bought the 5D body pretty well puts an exclamation point on that!)
Sooo, here's where my thinking is at:  EF 24-70mm f/2.8 L, either EF 70-200mm
f/2.8 L IS or EF 100-400mm f/4.5-5.6 L IS (probably the former for faster
speed), EF 50mm f/1.4 or EF 50mm f/1.2 L (probably the former, but kind of a
toss-up), EF 100mm f/2.8 macro.  To this I would consider eventually possibly
adding a wider f/2.8 prime (or EF 16-35mm f/2.8 L) and a longer f/4 IS prime,
but that's for later consideration.  Leaving out those latter two eventual
possibilities, and including the 85 already owned, that's five lenses, a
pretty full bag.  I don't like lugging and changing any more than anyone else,
but this seems to me a pretty reasonable starting point.  I figure the 24-70
and 70-200 as my walk-around tandem (probably the 24-70 alone if not carrying
a bag), with the fast 50 always there and available.  The others are for more
targeted situations, so in the normal course I'd leave them behind, although
would hate to be without the macro when some out-of-the-blue opportunity
suggests itself, which it often does, so maybe the 100 becomes a walk-around
component as well.

For what it's worth, I looked at the 24-85 and 28-105 EF alternatives in
place of the 24-70, but besides unwanted speed loss, reviews seem to favor
the 24-70 over the former, and wide-angle limitation defeats the latter.

As for herself and kids and grandkids, still have my little digital P&S for
family get-togethers and vacations, so no conflict with DSLR walk-around mass
where they’re involved.

Sorry for this being so long, but figured I'd answer questions before asked.
I’ll not be buying all at once, plan to start with the 24-70 and 100 macro,
and build from there, beginning with the 70-200.  Be brutal in your responses.
That way I’ll know I’ve walked on fire in arriving at conclusions, making the
inevitable “what if” easier to shoulder.  Thanks in advance for taking the
time.