How relevant are these distinctions and considerations to the selection of an "entry level / first-time / learning" SA?
It simply depends on what you want to do. Swept SAs were pretty much the oldest type of commercial SAs (FFT aka Vector SAs came much later due to the processing required), and as you stated correctly are generally the way to go if you need to cover large bandwidths (i.e. 2-25GHz).
If you don't need large bandwidths then a VSA becomes a viable option, and some of the advantages you listed (i.e. better for pulsed signals) can be pretty useful. And since VSAs are usually younger units they will statistically have more life left in them, and because they are fully digital they also support internal self-calibration and diagnostics which means they keep their specs for a very long time without requiring regular adjustments.
(On the one hand it's hard to imagine ever buying a second SA so it would be good to get a unit that will go the distance (5-10 years or longer?) but it's also hard to justify extra $ for something that is a nice-to have rather than a need-to have).
Honestly, how likely is it that any 30+ yr old SA you buy today, no matter how great, will still be in use by you 10 years down the line? Most of the stuff in those old boat anchors is already obsolete today, and most parts in it will also be pretty close to the end of it's useful life.
And frankly, with the relative low prices for some used kit it's in my opinion much more sensible to buy what you need now and, when you reach the device's limitations, to sell it on and buy a better device. This of course assumes that your first SA won't be a money pit which requires you to invest a multiple of the purchase price to keep it working.
Other considerations:
If you have a SA, a Tracking Generator would be pretty useful, yes?
If it's a swept SA, yes (VSAs don't have tracking generators because they're not swept). But again it depends on what you want to do. If you want to test cables, filters or transmission lines with a swept SA you'd want a tracking gen. Some VSAs like the E7495 which have an RF gen built in can do that as well.
I know, it would be good to start by pinning down some constant: price, functionality, performance, ease of use, reliability, etc.
A good start would be to think long and hard what you actually want to achieve, what bandwidth you need, and what parameters (i.e. specs, reliability, supportability) are most critical to you. And then you just filter the suggestions for adherence to your requirements.
As long as you haven't properly formulated your requirements I'd say follow joesmith's and Rupunzel's advice and try some sound card or TV tuner with SA software as a cheap learner. This way you're less likely to waste your money on something that's not right for you.