To follow my own advice, here's my experiment and the results.
7# pale LME
1# dark LME
0.5# homemade caramel
1# caramel 120
0.5# caramel 80
0.25# roasted barley
0.25# black patent
0.75# chocolate malt
2 oz Kent-Goldings
London Ale Yeast
OG: 1.063
FG: 1.016
I went to the LHBS with this recipe, sans the roasted and black, and 0.25# chocolate malt. I opted to use primarily pale LME because it's cheap as hell when I buy it in bulk. The guru convinced me that I'd need to bump up the dark malts to get the color and body that are characteristic of a stout, with the final result being what you see above. I made about 1/2 pound of caramel using some random recipe I found online (except I didn't add butter, milk, or cream, as the whole purpose of making caramel was for the beer).
Fast-forward 3 weeks: It's kegged now, and it's an amazing stout. However, the dark malts are quite strong, and absolutely mask the delicate caramel/toffee flavors I was hoping to achieve. If I had to do it all over again, I'd go with my original recipe (the 2 caramel malts and 0.25# chocolate) and not have worried about hitting an SRM above 40. A pound of lactose also would have helped achieve the desired results. The hops are barely noticable (as desired), and the yeast did pretty much what I wanted it to do. Also, I over-estimated my water usage, and ended up getting about a 5.5 gallon batch, hence the low gravity readings.
I have a somewhat peculiar habit of massaging my grains in a rinse bowl after steeping, so I can get a bit more color/body out of them. I feel that this greatly contributes to the thickness and mouthfeel of my dark beers, and really extracted a lot of color from the dark malts. If I'd have only rinsed the grains like most sane humans, the roasted/burnt flavors would not have been quite so pronounced, and my homemade caramel would have made more of an appearance.
Cheers!