I'd get the 2236. It's a better scope in every way. I have one and I love it, but then again, I dont have experience with the 4xx series.
These statements seem contradictory to me.
The 465 is older, but was build better / more expensive. The 465 probably has a better chance of surviving a drop (not that I'd recommend it) and will have a higher quality feel (not everyone that used the older series likes the 22xx series for this reason). The 2236 is newer, has more features, but feels cheaper. I'd expect fewer problems with the 2236 because it's newer, probably less issues with dirty pots/switches or caps. Everything equal, I would also prefer the 2236.
I would also consider the condition, seller, the amount of information the seller provides, any warranty, if I can pick it up locally / test it, if it includes a manual (though PDF versions can be easily acquired from places like
BAMA), if the probes are real Tek or cheap commodity probes and if shipped, how likely it is for the seller to pack well enough for it to arrive undamaged (not that trivial, since the front panel knobs are fairly fragile).
Professionally calibrated can mean anything from 'I took 30s to compensate the probes' to a fully traceable factory calibration, depending on seller. As long as it works fine, I don't consider calibration that important, since an analog scope is not a precision instrument anyway.
Re DSO, that has been discussed several times. If you can afford an acceptable quality DSO (like Rigol/Instek) now, it's a good choice (more useful for digital work), but otherwise, an analog scope will be very useful, even after you acquired a DSO (especially the cheap ones that don't offer features like persistence or high update rate of those costing thousands of dollars).