Well, SkyTools is the answer for the sort, but if you sort the SAC list by RA first, then by constellation, it pretty much will tell you the sequence to follow in a given constellation.
I don't know about you, but I tend to observe in one constellation at a time anyway.
Tony's idea of starting south and then heading north has merit, but only if you only observe for 2-3 hours at a time.
If you observe all night, the sky rotates quite a bit and new constellations cross the meridian.
So going back and forth from south to north to south and north again would be a decent modification of his plan.
The issue with Sky Tools, I found, is that it gives me a few thousand objects to observe each night and I can only see maybe 50 to 70 over a night (depending on the season),
and it's impossible to pick out which objects I want to observe in advance. Though perhaps it doesn't seem very adventurous, I tend to stick to my list of 2500 favorites or the 5500 objects in the Night Sky Observer's Guides
or "follow the herd" if there are other deep-sky observers there at the site. One of the nice things about group observing is that you may all select the same object and you can go from scope to scope to get different views
of the same object. One of the bad things about doing that is that you may enjoy using an eyepiece you don't own, and you know where that leads!
An 8" scope in dark skies can see up to about 15000 deep sky objects (estimate). Even being systematic about it, it would take many years to see all those objects even once.
And many objects you will want to revisit. Even though you won't see all those objects in bright skies, you might travel to dark skies or to the southern hemisphere, so, over the years, if you keep track of the objects you observe,
you will learn which ones to revisit and which ones not to revisit, and which ones you need dark skies to see and which ones you don't.
Sometimes just pushing yourself can be a reward. I observed 45 galaxies one night in the small constellation of Corona Borealis. Other nights I won't observe any objects in that constellation.
There is nothing wrong in using a variety of observing interests as they ebb and flow. You might look only at open clusters one night, and only planetary nebulae on another.
If you do it that way, the list size in Sky Tools gets more manageable. Don't forget to record which objects you want to revisit and which you don't. You might be able to see 15000 DSOs, but you may only ever want to revisit 1000 of them.
I guess the point is that there are a lot more than the brightest 500 objects in the sky to observe. Every night I think I've seen all the objects I want to see (and my log has about 13000 DSOs in it), I run across a new one I've never seen
that quickly gets added to my Favorites list.
I attach a small list of about 500 favorites I have seen in my 4" refractor. Your list might include other objects not on my list. I did not put objects larger than about 1° on the list so that people with SCTs and MCTs would still be able to see every object.
Remember to have fun!