You might have better luck with a stem/handlebar with a 26.0 mm clamp size instead of 25.4mm clamp size. I've retrofitted quite a few old school handlebars with modern aero brake hoods, and it is indeed a challenge with most of them to get a nice, ergonomic setup for riding with your hands on both the brake hoods and in the drop position. By the time "brifters" came into existence, most road bars had the 26.0 clamp size and so there's more out there in that clamp size that will allow a pretty good, ergonomic setup. Still, the modern compact bars in your lower photo are fast becoming the most common shape for bars on new road bikes. And for good reason; the ergonomics are ideal for most folks.
The best bars I've found to be used with a quill stem and "brifters" are these Deda's I found on ebay. They're deep, but the bend is such that you get a nice transition from the top of the bar to the brake hood, and still keep a nice angle for the lower part of the bar for riding in the drops. These handlebars are from the mid to late '90's, and were designed with the use of aero shaped brake hoods in mind. The stem is a 3TTT with a 26.0 clamp diameter.
