No experience with the Retro 50, but I love my OR50. Took a chance on it and bought without having played one before, sadly I've never seen any big (non-Terror/15) Orange in a store around here thats not a Rockerverb or Thunderverb.
Tone-wise its essentially a spongy Marshall. More vintage flavor than the RV/TV definitely. RV is nice but the dirty side gets too modern sounding for me as you add more gain. The OR50 just gets fatter and fuzzier. I usually keep the gain at like...12:30, just starting to hit the 2nd gain stage. First stage (0-noon) goes clean to a bit of breakup, quite nice cleans actually. Second is noon to 3:00, adds some thickness and fluidity. Nice midrange crunch without sounding stiff, its articulate but theres a pleasant bit of "give." Couple times I played a TV there was a sharpness that I couldn't quite dial out, the OR is a lot more balanced. 2nd stage is the place for most heavy sounds, its where I linger for my early doom/metal proclivities. The 3rd stage (3:00 to max) is just kind of ridiculous. Gobs of fat goopy gain there. I really don't go past 2:00 ever.
Good MV on here. I knew it was a keeper when I got better sounding bedroom levels than my old Tiny Terror. So I promptly sold the TT (sorta wish I kept it simply for ease of transport, but selling was the right choice tonally and a financial necessity). Generally I keep it around 10:00 for practice with the band. Played a show in a small warehouse type space last night and it was like 10:30-11. Kind of disappointed we didn't get any outdoor shows this summer as I'm still waiting to crank the living **** out of it. Someday. I don't mess with the HF Drive all that much, I probably should but I tend to just use it as a way of equalizing between guitars. Its essentially a presence control with a boost feature as you turn up. So my 2 main guitars with my band have Super Distortion and WLH bridge pickups respectively. With the Super D I'll keep the HF Drive at 1:00, with the WLH I'll go to 2:00. Compensates pretty effectively for the Super D's bump in output and crunchiness.
The footswitch is kind of silly. It takes the MV out of the circuit, which I guess they did to please some vintage-minded corksniffers. Nothing wrong with that, it sounds good when set up for it, but its completely impractical to be activated via footswitch because unless you're playing damn near cranked already and you pull the MV out it'll give a deafening boost in volume. This should've been a switch on the amp itself, would've made a lot more sense.
That about sums it up I guess. I hear nothing but great things about the Retro 50, definitely would like to try one at some point but it wasn't an option for me financially anyway. As it is I'm lucky I got the OR for the price that I did.
Let me know if you have any more questions, I'll make a point of popping back in here (rarely visit anymore, just a happy accident that I checked in today and saw this thread).