Thanks for the thoughts.
I feel there's quite a difference between conventional photography and astrophotography. With conventional, there are many more variables you can make use of. What is the weather like? The angle of the sun? Could you move around for different angles? With astro, when you can see it, you see what everyone else sees, give or take equipment variations. So in that sense, they are much more similar.
I have to say the first time I try something, even if badly, I do get a sense of excitement over it. Maybe I get better over several tries, but then it reaches the point where to get much better needs a more radical change. I think I'm nearing that point now. At what point do I draw the line on if it is worth progressing in. The webcam route is low cost. But much bigger scopes really start to add up.
Maybe it's more the practical side of things. I don't have unlimited time to image. My house isn't in the darkest area by any means. I don't know anywhere near (30 mins drive) I can get to easily that's much darker or clearer. It's cold. Weather is limiting and unpredictable. The last one is the biggest annoyance. My best moon image so far was taken on the 6th. Since then the sky has been quite cloud free at night, but I've not managed to approach that quality since due to all the movement.
So I think all things considered, I'm going to look at the webcam route. So unlike a DSLR approach, I'm not taking single shots that need to be great. Instead it will be practically uncomparable shots from which I can pick and choose the best. I'm exchanging high res high noise for low res low noise.
The money I could have spent on a bigger scope I'll likely point in the direction of the 5x macro lens in future... guess I like playing with extremes. Astronomical to near microscopic... might have to remember the bit in between now and then too.
_________________Canon DSLRs: 7D, 5D2, 1D, 600D, 450D full spectrum, 300D IR mod
Lenses: EF 35/2, 50/1.8, 85/1.8, 135/2+SF, 28-80 V, 70-300L, 100-400L, TS-E 24/3.5L, MP-E 65, EF-S 15-85 IS
3rd party: Zeiss 2/50 makro, Samyang 8mm fisheye, Sigma 150 macro, 120-300 f/2.8 OS, Celestron 1325/13
Tinies: Sony HX9V.