When shopping for airplanes like these, then, the search likely begins with a list of what is most important to you. Avionics, things like radar and deice, airframe age and time, engine time, other options, and paint and interior all have to be prioritized. No two shopper's lists are likely the same.
In doing a little vicarious Trade-A-Plane shopping, the V35B I would call about first is a 1976 model. It has had a Garmin 530 added to its radio stack and some other upgrades. It also has been upgraded with an S-Tec 50 autopilot. With 4,744 hours, it has been flown a little more than average but that's okay. The engine has 774 hours since a factory rebuild. The asking price: $149,500.
There are not a lot of mods or unusual options on the V35Bs in Trade-A-Plane. A few have tip tanks but the airplanes for sale are pretty much as they were born.
The B55 Baron I would call about first has a Garmin 430 and other acceptable avionics, including radar. It also has boots, which few of the B55s for sale have. An approved TKS system is also available in the aftermarket if you have to scratch that itch. This airplane has 4,010 hours with 150 since overhaul. It's a 1979 model with an asking price of $169,000. No mention is made of exterior or interior condition, so there might be some opportunity there.
Looking at E55s, which came along in 1970, the most appealing to me was a 1975 with low time engines and props, well-upgraded avionics including weather uplink and ground prox, full ice protection, radar and a lot of other extras. It has 5,030 total time and sounds like a fly-away to me, for $175,000. Ice protection is much more likely found on E55s than the other Barons.
So, there are a couple of Barons with better equipment for not a lot more bucks than what sounds like a desirable Bonanza. Choices. I would add that from the selection in Trade-A-Plane, the desirable V35Bs and 55s are likely to be in this price range. That 1979 B55 was the newest of those offered for sale. There are a lot of older and less-wise Bonanzas and Barons for lower prices.
Several advertised Barons that started life with 260-hp engines have Colemill conversions that include either IO-520 (285 hp) or IO-550 (300 hp) engines. These would give the airplanes equal or better performance than those built new with these engines. This could be an attractive thing to do at engine overhaul time, though, depending on 520 or 550, the complete cost of the conversion is either a little under or a little over a hundred grand. For about half of that, Colemill will put a 550 in a Bonanza, so that is another place where the twin can cost twice as much. (Colemill information is at colemill.com.)
Vortex generators are also on some of the Barons offered for sale. Personally, I probably wouldn't call about an airplane with VGs, but some folks love them and having choices is what it is all about.
As with all used airplanes, and especially ones the age of these, a pre-purchase inspection by a shop with experience on the type of airplane is extremely important.
To me, the choice between these desirable airplanes is as intriguing as it was when I wrote about it years ago. Some of the underlying factors, such as training and insurance, have changed, but the airplanes have not changed at all. The fact that Bonanzas and Barons are still being built speaks well for piston airplanes in this performance range, and if you think the financial step-up from a Bonanza to a Baron in either the new or used market is substantial, the next big jump in performance costs a lot more.