Chris, great read and even better to know you havent been put off by some of this hobbies eccentricities. I don't know if a dob should be on your shopping list just yet now and when you do maybe a 10" minimum would be what to aim for. A small dob is great to get you around the sky easy, eq mounts are a pain and you've found the kneeling position is sometimes a requirement depending where the eyepiece ends up. it's the little hassles that can cause first timers to just put astronomy in the "too hard" basket and give up. But it wont be lng before you go chasing those faint fuzzies and seeing a galaxy through the eyepiece is just amazing I hear (never have yet with my gear and my eyes). And for faint fuzzies the width of your light bucket is important not so much its length (another bumper sticker in there somewhere, a kickstarter opportunity perhaps to buy more gear, um research tools?), but with a reflector and refractor you're set for years to come. At this point I would suggest some good quality eyepieces be on your shopping list as the ones supplied with a scope are poor quality and your view will sharpen up with crispen and more contrasting views with some quality eyepieces, Again I'd keep away from the eyepiece kits as they will be a small improvement but in the long run a wasted money stop gap. I'd suggest a Baader around 8mm and 24mm and maybe a quality barlow (I got the Televue Powermate 2.5x I think to use with Baader Hyperions (now superceded by their Morpheus range)).the will give you a good spread of "zoom", some of the lower end scopes dont like achieve focus with a Zoom eyepiece (I use a baader zoom mostly when visual) but cant say for certain to buy it yourself with your scopes. You'll see yourself a good eyepiece will seem like you bought a new telescope, keep your eye on the sales section as others sell off their good eyepieces, televues tend to vanish fast. But try to calm yourself and stick to two good eyepieces at the start with good eye relief. I'd say one around mid20mm to 30mm as a wide view (for larger regions, moon, star hopping etc) and one around 8mm (maybe 6mm) as your closeup zoom eyepiece for planetary and craters. Problem with sub-10mm eyepieces is the atmospheric seeing conditions quickly blur the image losing you detail becaue the magnification factor is high. I found my 8mm hyperion was reliable for crisp viewing and on good nights with the powermate it becomes a good 3.5ish mm eyepiece. Avoid the cheap barlows off ebay, they use plastic optical elements (like some of the cheap scope supplied eyepieces), aim for a quality one and buy once rather than work through intermediates wasting money on the way. You dont need to make rush purchases, You may be able to get a little time on someone elses telescope one night and try your good eyepieces with a good barlow and see if the difference is worth the cost. Once you hit seeing limits your gear cant improve matters . I'm sure others have differing opinions though, I still consider myself a newbie with many years and dollars under the bridge in this addictive hobby
Still learning every day and enjoying it. On the subject of seeing, somebody recently posted a link here to an awesome seeing guide site that I've forgotten. Worth trying to get your head/eyes around judging seeing so you dont go buying gear you cant use when the seeing limit is the problem (unless you can launch your gear into space and away from our dodgy atmosphere.
The sky is a big place and always something to see. You may find yourself being draw for some unknown reason to just certain aspects of it. Maybe a messier spotting list: see how many you can see each year. Comet hunting, binary splitting, a lot of this stuff sound boring on paper but once you hunt down something and get it in your eyepiece its a weird thrill, we all get it so dont feel ashamed. I still need to get uranus and pluto in the eyepiece one day, no hurry though, been a few years since I tracked down neptune with a 100mm tabletop dob. using both a tablet app and star chart book and 45min of slow methodic star hopping, being certain of my view until finally there it was a tiny blue dot lost in all the other dots and the only dot not accounted for in the star chart and just where my tablet said it should be. Jupiter and saturn always still thrill me, i'm yet to see the red dot through eyepiece though. The sky is there for you to explore at your own pace and in your own way.
Dont forget the sun either, sunspots are easy to view and photograph with a home made
baader white light filter. If there's no eclipse coming up pick yourself up a batch of five or ten eclipse glasses off ebay to share with your mates (just for looking up at the sun, NEVER to be used with binoculars/telescopes/monoculars etc). Partial eclipses are more common but still infrequent and still amazng to see with your eyes. Just be aware if there is a total eclipse coming up somwhere on earth, the prices go up and stocks vanishe fast. Worth picking up a few when you can just to have on hand. You can make your own camera/telescope solar filter for shooting sunspots using the baader solar filter sheets I linked above and a few plumbing bits. ONLY use the Baader sheets though, alternatives using equivalent mylar orwelding glass might work but it might also damage your eyes and equipment too, the baader sheets are around $40 for A4 sheet and the right tool for the job.