I'm just learning about DSOs and I'm not finding the transition to be difficult. I still only twiddle 3 things: Volts/div, Time/div and trigger polarity/level. That's all I need from a scope. All the other stuff is interesting to look at but not terribly useful - to me. As a guy who plays with FPGAs, uCs and robotics. Sure, I like the 4 channels but I got along for a long time with just 2. I bought the 1054Z specifically for 4 channels and the idea that I ought to expand my horizons.
But on the bench, I twiddle the same limited set of knobs that I used on the analog scope. In some ways, the menu system is slower. I actually have a 'switch' on my analog scope to change trigger polarity. I don't need to fool around with a menu. Trigger level is more intuitive on the DSO (it draws a little line) but both work the same. There isn't any difference in Volts/div and Time/div - just twiddle the knobs.
I just don't see my having learned on an analog scope as a handicap. Same knobs, different colors... In the context of this lab, finding RMS, P-P, FFT and all that stuff is useless. Now, the pulse width measurements will be handy but, really, that's why the graticule is there. 500 uS/div, 3 div wide pulse -> a 1.5 mS wide pulse which ought to center the servo nicely. In such a system, measuring the width to 3 decimal places is useless. "About" is close enough!
I know I'm swimming against the tide! As I look at multi-thousand dollar analog scopes being sold for $200 or less I get the idea that the market is rather limited. Everybody wants a DSO!
A downside of getting some analog 'scopes is that you would be unlikely to pick up four identical ones.
The other thing is that good brands are old,affecting reliability------you can still buy new analog Oscilloscopes,but they are fairly basic ones,& are very overpriced.
School lab 'scopes don't need to be spectacularly good------the Cossor things they had back in Tech School were very far from "state of the art",even in 1960,but we learnt the subject using them OK.
I think I would go with the Rigols---the OP may get a discount for buying four.