and the sun and the moon the cheaper telescopes are great. Some even for photography.
the DSO's are the problem. I have a very decent Catadioptric that I used to use until I lost some parts... but, it was just slightly under the recommendation for DSO viewing. What I'm getting at is what you said.... "it all starts to look the same after a while"... and that's true unless you take that step up to the DSO rated telescopes... where things like nebula really start to 'pop' and resemble those astro-photos we see posted.
Of course you 'can' see some Nebula, Binaries, even with the cheaper telescopes... but they do not 'pop' and I think you're right... it would get boring quickly UNLESS you're obsessive like me.