Once you have become fascinated with the night sky, you want to share the view and that gets you on the road towards astro-photography. This road leads to many different places and you can explore all of them. I have a few recommendation to gradually improve the skills as one step provides experience for the next

1. just simple unaided visual observation is amazing if you find dark skies
2. wide-field / landscape astrophotography is a good starting point with great results and you don't necessarily need new or expensive equipment
3. some people like to add startrails to that
4. incorporate the moon
5. try close-up shots of the moon with a long tele
   -- that will show you some of the challenges you'll face if you want to peek deeper into the sky
6. now your better prepared for the galaxies far, far away

If you want to get a closer look ad the deep sky, many think about buying a big telescope. Before you spend that money, I recommend to first to recognize the following (from my own experience)

• While a simple landscape shot at night can be as quick as ~3 minutes (1min tripod setup, 1min exposure, 1min packing up), once you decide to use a motorized (tracker/telescope) setup, every shoot will take much, much longer. North-align, batteries, cables, multiple long exposures, ... with a SLR + 50mm lens you'll be a bit quicker than with a 20lbs telescope. Many of the steps still remain the same
• light-pollution near our cities is very frustrating -- it takes me at least an hour's drive one-way to get onto some nearby hills to sit at least above the most intense glow.
• the increase in magnification from a tele(scope) means, you also see more imperfections -- from cloud layers, atmospheric distortions, color-fringing,
• there's a lot more to learn compared to a "simple" landscape shot, often using additional SW & post-processing to reduce above mentioned imperfections
• And exposure times and the necessary times for post-production are much, much longer than the quick 30s landscape shots.
• not all astronomy accessories will fit instantly -- you'll be surprised what kind of adapters exist and even then, there are combinations you never get to work
• some telescope setups are bulkier than others and the size of these transportation boxes can be stunning. Measure the size of your trunk before shopping for a mobile setup.
• some telescope-types require more maintenance than others -- an issue often overlooked by beginners.
• I wouldn't call this hobby a bottomless pit -- but if you want you easily can spend high 5-figures just on a up-scale telescope mount. The ~$800 GOTO mounts are very capable, $2000 to handle heavy telescopes.
• Most telescopes are far less expensive than SLR super-tele lenses like the 600mm !! $2500 buys you a 70-200 f/2.8G VR-II or a 10" Reflector or a deLuxe, Carbon-fiber 5" refractors -- for ~$1500 you can get good mid-range scopes. Of course there is no upper limit and you can find telescopes as expensive as a luxury SUV or more.
• In addition to the mount & telescope you want to factor in a couple of hundred dollars in various extras (finder scopes, eyepieces, guide-scope & camera, ...) You won't need them all at once but it is worth mentioning it to avoid surprises

Instead of rushing and buying a big telescope, buying a good motorized telescope mount is a better option, since you can use that together with your existing cameras, teleconverters & tele/zoom lenses. Use it with a wide-angle + motorized mount to AVOID STARTRAILS :-))

I know, despite all this, you still have set your mind on getting a telescope -- I don't blame you :-)) In the posts that will follow, I will comment on the rational behind the various choices I made. Those are sometime very subjective choices, and you may disagree or find too expensive. I'll state my reasoning and you can make up your own mind to draw your conclusions.
Also some of my choices were made 2 years ago and by now, better solutions are available

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PS : sometimes I will mention a brand or a particular model -- I'm not affiliated with any of those. Usually I use those references as examples. Not as a buy recommendation, though some of these example I bought myself.
And similar, if I say I don't like XYZ, I will state my reasoning with pros & cons. Feel free to disagree and buy it anyway.

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