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Okay I will take a stab at this. It does not have to be 4+ hours a week. It could be 2 hours every week/week and a half/two weeks. Personally, I would call it playing D&D online with friends.
1. You can use Discord to chat, which I have done and add pictures to it. You can talk, type or both. You might want to go on youtube and read up or watch games utilising Roll20 or tutorials for Roll20. Do not think of it as acting, just know what your character is about, what motivates them and let their actions and choices speak for itself. Just do it slowly and gradually, it does not need to be full blown theatrics out the gate. I’d gently encourage at least having a character history and motivation. Otherwise it is kinda just a different miniatures game. Do whatever works for you though.
2. Only use them for when its needed, messy, clunky or positioning really counts that much. I would say run a few small games, get stuck in, and get a feel for yourself with some experience and trial and error of where you are at and what is next.
3. This isn’t really a question and I am not sure what input you are looking for on it. Maybe don’t do that if its something you are worried about happening again in future? Also, just play 5th ed d and d.
4. D&D Fifth Ed is more streamlined and fun. Its different to earlier editions so don’t expect the same thing with levels and meta. Loads of options in this edition. Some people complained it is not hardcore enough and do easy to not die (you can always change that as DM) but it is the most widespread, popular, successful and liked version if the D&D 5th Edition facebook page is anything to go by. It is more like 3.5 than 4th. 4th ed was terrible. I gave all my 4th ed books into a second hand book shop. I’ve played a lot of stuff. Too numbery. I’ve heard of some people enjoying it but it was in sharp contrast to the overwhelming dislike in the general consensus. Low level D&D can still kill you but it is not as lethal, not that I have played 2nd ed it is just from what I read and hear about. Lots of built in class options. Characters can be powerful enough in the second tier of adventuring levels.
5. OOC what are you actually, more specifically looking for because you mention 2nd ed with fondness a lot and you seem to be leaning into that heavily. Do what you want, and what works for you guys and makes you happy if your content you got all the stuff. Personally, D&D as a miniature game is a bit of a flat experience that misses the point, regardless of edition. The only people really needing to spend is the Dungeon Master and after a year of play if people do not want their own players handbooks then I would raise an eyebrow if they are really invested. Regardless the 5th ed starter set is inexpensive and full of great content.
6. There are a lot of adventures and campaigns out there, both official and not official so there is no shortage of material to draw on if you do not want to write modules. I encourage people writing their own adventures; imho a RPG shouldn’t be balanced because it’s a living and breathing world. Even then with pre-written campaigns players will always always always come up with things that can’t be predicted. So, that last bit is a hurdle you can only overcome with reacting and improvising.
7. The Starter Set, Lost Mine of Phandelver is a great mini-campaign with four or five sections of varying length for levels 1-5. I’ve run it five or more times for various people of different gaming experience and it is solid. If they are new to RPGs and you are worried about attention span start with a nice, accessible, understandable, relatable and Tolkienesque setting like Faerun/Forgotten Realms for Dungeons and Dragons. The less complicated moving parts the better.
8. D&D is nice and simple: roll a 20 sided dice, add a modifier, beat a target. It is simple and a better known system. Even if the editions change that is the crux of all of the editions. You fail or succeed. Again, fifth ed d and d has a lot going for it.
Most of the campaigns have blrubs about starting at level 1, or continuing on from the starter set, or continuing on from other campaigns so it is pretty tight. There is also the D&D Essentials set which has an adventure in that which I have not got around to yet. All the campaign books tell you what levels they cover as well on the product description or back of the book. If things fall apart after a few sessions that’s not on you or how the campaigns are written.
There are lots of other systems out there but D&D 5th ed, to me, is the most fun, least convoluted, satisfactorily detailed, and material rich system to work with due to how it has exploded in popularity as well as my own personal experiences. I think because of roll20 it lends itself better to games online, but no, no game system is better or worse for online play. I think it is down to whether it is a good system or not.
You mention it not seeming the best, but I mean, if the game falls apart after 2-3 sessions you aren’t going to get anywhere remotely near level 12 if you start at level 1. My players spend about two and a half years, I think, going from the starter into Storm Kings Thunder campaign and didn’t hit level 12. Close, but not 12. And that was consistently playing one night nearly every week for 2-4 hours, roughly.
As for anything else you should be considering, I think you should make a more concise list of what the needs are for yourself or whoever the DM is as a DM and another for your players and reassess what you really want, are looking for and how to accomplish it.
I hope this helps.
