I might have some insight for you.
If you're considering that vintage a car, my brother owned a '49 Olds sedan for several years, 6 cyl, 3 on the tree. He even used it as a DD. A nostalgia fueled purchase. (he was born in '49) Yes, it's a highway cruiser, but don't expect to break the land speed record in a 6 cyl. American car of that era. I drove his Olds occasionally, and I enjoyed it for short rides. It'll cruise fine at highway speeds, just be patient getting up those speeds. A camry will dust you. It was insanely roomy, and easy to work on, and even got decent gas mileage, but the specialness wore off quickly and it became a somewhat tedious car to drive, with minimal creature comforts plus it did nothing particularly well by modern standards. The combination of non power steering, (ie. heavy and numb with play ), drum brakes, bias ply tires (you think your t/a understeers?), balky column mounted shifter, unsupportive bench seats (though fun on dates
), heavy weight and docile 6 cyl motor was not a recipe for excitement by any stretch of the imagination. If the 4 door chevy car pictured with the side pipes is a 6 banger, a baby boomer car guy might see that as an oxymoron. It was seen more as a "mom-mobile". Now a V8 in a 2 door? different story. They had a bit more pep, sounded better, making it a bit more interesting in a straight line and thus more appropriate for leg pipes. But they all were what they were: not very good. That's why you can still buy them so reasonably, especially the much less desireable 4 door models. If you wanted something sporty that handled better, you looked at European cars back then. IMHO, Unless you have an emotional attachment to early 50's sedans, or love going to cruise nights, I'm not sure I'd recommend buying one.
As far as drum brakes, Yep, drum brakes are not as good as disc, especially in the rain. But you should not be fearful. the stopping distances are longer (and no ABS) but they still stop fine in normal driving if you don't drive like an aggressive fool. Heck, My first 4 cars had drum brakes. It's no big deal, especially if you drive patiently and look farther ahead. You'll probably find yourself coasting a lot more in those old powerglide Chevies so you don't have to pound on the brakes so hard, but if you need them in a pinch, trust me, they work. I'd advise against long track sessions w/drum brakes, But keep in mind old racecars used them.
regarding the 2 speed powerglide, they were great. very durable. I had a '65 corvair with it (knucklebuster dash shifter), and my aunt had an early 60's impala with it for many years. Very much for highway cruising. Since there's no overdrive, the engines rev higher than you're used to, but not as much as you think. They were not high revving engines back then. The only downside to the powerglide in my corvair was the lack of "park". you had to use neutral and the parking brake. And common sense dictated when parking on a hill, you turn the wheel enough that the tire hits the curb if the parking brake failed. You might see your parents do that instinctively if they still parallel park. That's simply what you did.
As far as summer cruising? Uh, no. Evening perhaps, but not summer days . You'll quickly learn there's no a/c, not even dash mounted vents. The only vents it does have cools only your ankles, and you'll desperately try open those little triangular vent windows as much as you can in the summer to get more fresh air. That's also why I'd only take one to a cruise
NIGHT, not a cruise day.
Fwiw, my dad bought a then new '51 Chevy fastback 6 cyl, 3 on the tree. (similar front end to your picture) I was too young to drive that car. He always said he liked it for it was (reliable family hauler of it's day), but he did not consider it a fun car. (His Jag filled that role). Hope that helps.
^