Just reflecting that, given the time investment involved, it probably would have been better to get the 10" Dob to see the DSO's just a little bit more clearly.
I guess a benefit right now too is learning the maintenance and care aspects on the 8".
That said I'm very much enjoying the visual astronomy part; just went out last night and got a bunch of more messier objects checked off on my list.
There will always be that issue of just a bit more aperture and my views would have been just a bit better. That's enough to drive some (but not everyone) toward ever greater apertures until finances, practical use/storage/etc. issues force one to a stopping point.
And yes, smaller, less expensive telescopes present less risk for all of those inevitable learning mistakes that one will encounter when starting out. That's something that many learn the hard way. Many focus only on the "seeing more" aspect and end up blindsided on the negatives of going larger.
Haven't checked off all the Messier objects yet? I gain the impression that you're still in the "looking at stuff" phase as opposed to the "observing" phase. The difference being one of taking the time to see more in the way of details within any given object and more in terms of picking out ever fainter details/objects with what one has. Once one enters the observing phase, one will start seeing more with what one has -- without having the need to utilize more capable equipment. One, in effect, becomes a more capable observer thereby gaining the ability to see more without upsizing one's telescope(s). Instead of checking off multiple objects during an observing session, one might very well spend two or more observing sessions concentrating on just a single object.
I've not kept track of how long it's been, but it's been many years since I've felt the need to use a telescope greater than a 6-inch aperture. For me, the possibilities and what I can see with 6-inch and smaller apertures are great enough that I have no desire to look through a larger telescope (and I have larger telescopes -- a 10-inch and a 12-inch). I could draw my own limit at 130mm and still not feel that I'm losing out by not going larger. (My 130mm scope, an Astro-Physics apochromat, is for most of my purposes superior to my 6-inch scope, an f/6.5 achromat. But nevertheless, I still enjoy using that achromat.)
One can go further in this hobby by going with more capable equipment. But one can also go further by increasing one's own skills. Some choose the first approach. Some choose the other. And some try for some combination of those two approaches.
In the end, it's whatever makes one happier, and that's not the same thing for all of us.
I think you've done well in choosing and using your 8-inch telescope. Where (or if, or when) you go from there is entirely up to you. But there isn't one path to follow that's going to be "best" for everyone. There are simply too many variables that can affect one's chosen path. One path can be better for one person while a different path can be better for another. So, in these forums, we often see different opinions that can quickly erupt into heated debate.