An 8" Dob is a great way to start, but if you're financially constrained, then a 6" is allowing you to have some change for bits 'n pieces. But, you really don't need all that much extra to enjoy visual observing. You will get a few reasonable Plossl eyepieces with a Dob purchase. Collimation can be done without an expensive laser. All your sky software & charts that will get you going can be obtained freely off the web.
If you go to 100mm, it will double the aperture from your 50mm, but quadruple the light-gathering. If you get the 70mm refractor, it will increase your aperture by 40%, but nearly double your light-gathering.
Personally, I wouldn't go below 6" for my primary scope, but if it's something you would keep when you upgrade, as a grab & go, then maybe!
You can always get better eyepieces and use them with an upgrade scope. Don't get too fixated on accessories, you can do some very rewarding visual observing without too many extras.
Cheers
John
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