I am not much of an astronomer but I have had and have both (not Skymasters though) and my favorite are my stabilized Canon binoculars. Very portable. I can just make out the rings of Saturn and Jupiter and moon is glorious. I also have large binocs but the problem with them is that the straight through viewing is difficult when viewing objects high overhead, which seems to be often. Though you could get counterbalanced tripod for binoculars. Binocs with angled eyepieces would be ideal but expensive. Also difficult to take photos with binocs.
I also have the Orion ST80 and once I added a 2x barlow it was perfect for me. I also got a variable power eyepiece because I was tired of switching out the eyepieces. Better views of planets, not perfect on other objects but usable. Probably very important is to get a decent tripod (counterbalanced is pretty cheap) with fine adjusters as a standard video camera tripod is difficult to aim.
Also portability is an issue. If a scope is big and heavy, you won't want to pull it out. I currently use my spotting scope and love it because it is backpackable, uses camera. Doesn't take up much room in our apartment. But not great for looking at deep sky stuff.
My 2 cents.
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