What's the Cheapest and Best Way to Get Started?

I bought in to a rival virtual tabletop with an ultimate license and core rulebook for D&D 5e. It had a steep learning curve for me as DM, and I basically never used it even though I needed a way to play online with old friends across the country. Now I no longer have a computer that is compatible with that particular VTT and several of my players don't either. I'm thinking that a web-based alternative with Roll20 might be better for us to all connect and be easier for me to use.  But before I sign up for anything, I don't want to repeat the mistakes of the past with that other VTT. I want to try it out, make sure it works for everybody, and make sure I can do with it what I want.  Do I need to purchase the D&D pack? What level of subscription is needed to host a game that works? I want to see the bells and whistles of Roll20 but not be out over $100 dollars to do so. Like, could I get the D&D Essentials Kit and run a game just off that - so my friends and I can see if it works?  

You do not need to purchase anything to run a game on Roll10. Yes the bells and whistles add to the game but they are not needed. You can upload your maps and tokens. You can open empty character sheets and hand fill them in. You can use the fog of war to block off map sections so you can reveal them later. Paid subscription (5 or 10 a month or yearly sub) will help automate some or most but that is not needed. Purchasing of marketplace assets cut down the work but it is not needed if you are willing to do it yourself.

These should help: What Should I Know About Roll20? - short video Roll20 Tutorials - list of good roll20 tutorials Helpful Roll20 links

I know I *can* create my own adventures, scan maps, create assets, program macros, etc., but I'm looking for the absolute most beginner friendly way to do this. I got so burned out trying to work with this other VTT. I spent literal hours trying to make a simple encounter that still turned out like trash.  So the hierarchy of need is: 1) working well for all the players; 2) easy on me; 3) affordability. [I just don't want to break the bank just to "try out" a system, if that makes sense.] 

I ran my first campaign for 6 months on the free version. Upgraded to Pro ($10/mo) eventually for the lighting system and some of the other features. Program has steadily improved in value over the last 4 years. I play 2-3 days a week on this platform now with different groups of players.

Some points to consider about a free game: You have resource to everything that is in the SRD , in way of classes, races, spell, monster and magic items. You can run a perfectly workable (if limited) game of D&D with this, only manually filling in the items that are not in the SRD. Since the SRD contains no art, you will need to provide your own tokens and maps. Roll20 gives you a limited selection of those, but there are plenty to be found, even with a google image search. You will need to link any tokens to their respective character sheets. A free game contains no dynamic lighting. You will need to do your own hiding and showing with regular fog of war . My suggestion if you want to spend minimal money, but still get a good feeling for what the system looks like once you have spent some money is to buy one of the small modules from the Tales From the Yawning Portal . They are only $5 each, and come with all the monsters, tokens, and maps for the adventure already pre-set. Note that features normally unavailable to a free user, such as Dynamic Lighting, remain unavailable, though the modules are set up to use these features if you do have access to them. My recommendation would be Sunless Citadel for beginning characters, but that's up to your needs and preference.

For an absolutely free sampler as a start point I always recommend  The Masters Vault

Top advice, click "Create Game" (FREE) and check it out. Draw a map that is 1 room (square box) and 1 hallway.  Go under Journals (where the character sheets will be stored). Click ADD Character. Look at your first blank character sheet. Fill it in. All of this is Free. Type something in the chat room. Try rolling the dice. It's all free.  Invite 2 or 3 friends into the game table (use the Invite feature). Do a chat with them in the game table. Try the voice connection. Try the webcameras. Show everyone the map you made of a single room. Put some "Tokens" (miniatures for the PC) on the map. This is the best place to start, for free. After this free test you will be able to decide if Roll20 would be worth the efforts to run your campaign. Second-best free starting point will be "The Master's Vault" a free 5E Module on Roll20, which Z said.  Click "CREATE GAME" and choose Add Module: The Master's Vault. Now open your game you created with Master's Vault. Enter the game table. Click the different tabs. Read the handouts. Try the tokens. Invite your friends into the chat. Let them move the tokens. All this is another free option which will show you more about the "automated" 5th Edition D&D features of Roll20. Ryan H. said: I know I *can* create my own adventures, scan maps, create assets, program macros, etc., but I'm looking for the absolute most beginner friendly way to do this. I got so burned out trying to work with this other VTT. I spent literal hours trying to make a simple encounter that still turned out like trash.  So the hierarchy of need is: 1) working well for all the players; 2) easy on me; 3) affordability. [I just don't want to break the bank just to "try out" a system, if that makes sense.] 

New Roll20 Player/DM here. To continue this line of questions...What would be the best case scenario for the following. ( There is probably similar questions out there) Transferring 2 in person campaigns to online Roll20 (have all books). 4-6  Players 2 campaigns with 2 DMs (DM 1 - Avernus: about to go to next chapter; DM 2- ToA: Just about to start), Want easiest "full feature" setup with lowest price point. So taking this into consideration, the questions (and guesses) are First, which "books" would I need to purchase for ease of setup and tokens? My guess is PHB, Xanathars,  and the 2 campaign books. Do I need the monster manual bundle? shouldn't campaign books have all needed stat  blocks, tokens, etc..? Second, if I buy the above books on one account and get pro level membership, will the others in my group be able to take advantage of all the features and can I delegate a second DM to run the other campaign? What features would the other players miss out on? Thank you for taking the time. Stay safe

Not sure what you mean by "the two campaign books". Ravnica and Eberron? I'll do my best to answer. Players would most benefit from PHB, Xanathars and Volos, for the greatest number of character and race options. There are a few other options scattered here and there, but that's the bulk. The Monster Manual (and to a lesser extent Mordenkainen's Tome of Foes will get you most official monsters. Again, there are some scattered here and there, and there are some sourcebooks that will give you a ton of un official monsters. If my assumption about what you mean by campaign books is correct, you will have everything that is in the print editions of Ravnica and Eberron. All monsters, classes, races, spells, etc. They will not have anything that is only referenced  in those books. For instance, if the print edition says there are zombies in the Land of Jo, but contains no statblock, there will be no statblock in the book. (Fortunately, there are zombies in the SRD.) Any module will have all of the monsters, maps, etc, needed to run the module. Second part: The cheapest way is for one of you to get a Pro account ("to take advantage of all the features"), and be the creator of all the games your group plays. Once you have created a game, you can promote another group member to be GM of that game, and rejoin as a player. They would have nearly all of the rights of a creator, save the ability to add addons (you would need to do that for them) and a couple of largely administrative powers. All players would have access to compendium resources (PHB, MM, Xanathar's, etc) to the limit of your sharing slots. The group size you posit easily can share one sharing slot (one per game). Our group of 5 has four different GMs who each run a game on my account, so I have one sharing slot left over, for instance). I am the only one who can create a game on that account, so I need to be the owner of any module or addon that is used. The players will not be missing out on anything