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This one is going to be long-winded so I apologize in advance :)

I have been DMing D&D for a really long time. I have been DMing D&D and Pathfinder on roll20.net for a while as well. I dumped all other versions of tabletop (at the moment) for D&D 5e. D&D 5e moves away from the spreadsheet stat crunching type of play that D&D 3.5 and Pathfinder embraced. D&D 5e also departed the mechanical MMO style play of D&D 4e. I think you are making a good choice in choosing 5e especially being a group of new players & new DM.

Here are the things you'll need to make roll20.net work well:

• Everyone will need a free roll20 account
  
• Everyone will need skype,teamspeak,ventrilo, or google+ hangout capabilities to talk. Trust me voice chat is much easier to interpret than typed chat available in roll20.
  
• Everyone will need a really good imagination and patience as you all learn the ropes
  
  Since you are all new, I would recommend running the Lost Mines of Phandelver. It is included in the D&D Starter Set (On Amazon for $12). It is an adventure that will take a group of 4-5 players through level 5 (roughly). I ran this for a group of newer players and it took us roughly ten 4-hour sessions to complete. The set comes with some helpful things for you as the DM and them as the players. It comes with the basic rules for both the DM and the players. These are also available and updated through Wizards of the Coast for free as PDFs and browser-friendly sources. It also comes with some pre-made character sheets. These are handy as they can save you time (and money) from generating your own characters. Usually for 4 players, it can take an entire session to plan out a character for each of them if you are new. This can give you all a taste of how the game works, how characters work, and if everyone is on board. Totally optional though! The adventure itself contains a DM booklet that gives you tips as a new DM as well as maps, layouts, monster stats, and descriptions.
  
  On the subject of maps and roll20. Roll20 gives you a graph-paper view that takes up most of the layout of the app. There aren't many gridded, digital versions of the maps for 5e adventures that I have seen. The ones that do exist will cost a little bit of money. This artist sells both player and DM versions of the maps for the adventure, but leaves some of the smaller encounters out. 5e relies on a lot of mind theater and imagination on both the players' and DM's part.
  
  What I tend to do for maps is, use the graph paper and draw on it using the simple controls roll20 provides. I tend to do this when I can't accurately describe the way things are laid out. For instance in the Lost Mines the first encounter can be tough to explain so I drew a rough outline of how the map looked while explaining to the players where they were, and where what they saw was.
  
  I'd highly recommend you get a free account at roll20.net first and then log in and play around with it, just to see what it handles like. It has its quirks for sure.
  
  Aside from the Lost Mines of Phandelver, there is one other official campaign called the Tyranny of Dragons. It contains two adventure books, Hoard of the Dragon Queen and Rise of Tiamat. They take a party from levels 1-8 and 8-16 respectively. Hoard takes a lot of skill to run as it is a bunch of loosely related occurrences that clever or adventurous players might want to explore outside of. It doesn't provide much support to a new DM for handling this. Rise of Tiamat opens up a little more and is easier to run but without Hoard, it can be confusing as to what is going on.
  
  Drivethrurpg has some smaller 5e adventures available. I haven't played any myself, but I have heard some good things. They are located under their D&DNext/5E heading.
  
  If you decide you do like 5e or are really committed to the cause from the get-go, I would recommend any player and the DM get the Player's Handbook (Amazon). This contains the rules governing attributes, player creation, combat, downtime, and a full description of all spells and spell casting classes. It goes well above and beyond the basic rules for players and I feel it is truly necessary to having the full experience. It can be pricey if you end up not liking it though.
  
  The DM additionally should consider the Dungeon Master's Guide. It really helps in running adventures, giving good flavor to the game, and creating your own campaigns. The Monster Manual is an optional buy, but helps by giving a large list of classic D&D monsters to populate your game with.
  
  I'm guessing you have already found /r/DnD, but for 5e you might want to consider /r/dndnext which has weekly question threads and is more focused on 5e (which was previously codenamed next).
  
  tl;dr: Whatever you end up doing, just make sure you and your friends agree that it is to have fun. You don't need to be perfect with the rules and you can feel free to make mistakes along the way as long as you all agree to laugh it off. You are playing with your players as a DM and not against them! Good luck.

I think /u/NecronosiS nailed most of the important stuff, but I'll add some things I've picked up as well.

• When it comes to DMing I've found that I take bits and pieces from each person that throws suggestions my way. I like the way this person does this particular thing, and the way this other person handles this particular aspect of the game. When to and not to use things, how to handle situations, the game is so much in your hands that each DM is a very individual beast.
  
  
• When it comes to deciding on how to read a rule, there are times where as the DM I just decide this is how it is and stick with that. There are other times I ask for a consensus from the players on how they want to play it, making sure they know that it will work this way for both players and monsters so that if they just choose the most favorable outcome for them it could come back to bite them in the ass later.
  
  
• As for which adventure to start with, I've found that the Lost Mines of Phandelver that comes with the Starter Set ($13.50 on Amazone right now) is great at giving players and DM's a window into all the various aspects of D&D 5E. After they play it for a little bit they'll be able to know which aspect they like better and that can guide you on what adventures to run in the future.
  
  **Ninja Edit

Welcome! And, just in case, one thing you need to consider when shopping for a laptop to be used with skype/discord, or whatever, is what kind of headset or headphone/microphone setup you plan to use.

Quite a few modern laptops have a single combination 3.5mm audio/mic input. If this is the case (like with the higher-end ThinkPads), you may need an adapter/splitter like this to use a standard analog headset that has separate audio/mic cords.

Some laptops still have separate audio/mic jacks. Standard headsets or a headphone/microphone setup with separate audio & mic cords will work fine.

If you use a USB headset you don't have to worry about any of this, as they'll work as long as you have a free USB port.

Personally, I use a pretty cheap (but decent!) headset here that has separate audio/mic cords. My smaller X201 laptop has separate jacks, but when I use the headset with the combo jack on the T430S laptop I just use a splitter.

Just FYI!

I run the roll20 app inside of google hangouts. It does the game table, and voice chat all in one window. I have tried every chat client out there and Hangouts is by far the best now (it sucked the first few years, but it is google so it got fixed).

On another monitor I have our campaign document open, which is a GoogleDoc spreadsheet with a tab for every character and several game notes. I share all of that in a gDrive folder with the game rules and handouts.

I keep a pdf of the gamebook open on a third monitor (I only use pds anymore so that I search the text).

Then I have also started to run Roll20 on my tablet as a player so that I can make sure I see what the players are seeing.

A good microphone

http://www.amazon.com/Blue-Microphones-Snowball-Microphone-Headphones/dp/B003LRTQEA/ref=sr_1_14?s=musical-instruments&ie=UTF8&qid=1410961646&sr=1-14

And webcam

http://www.amazon.com/Logitech-Webcam-Widescreen-Calling-Recording/dp/B006JH8T3S/ref=sr_1_1?ie=UTF8&qid=1410961712&sr=8-1&keywords=hd+webcam

We started about a year ago with the D&D Starter Set. It has an abbreviated version of the rules and DM Guide, some dice, some pre-made player sheets, and a campaign that you can do to learn the game. It's been a great experience.

Good luck!

If your more comfratable hand drawing maps you could always get one of those hand drawing usb things (like this http://www.amazon.com/Docooler-Graphics-Drawing-Cordless-Computer/dp/B00F33URN4).

Should be as close to old school pen and paper as you can get.

For conventions where I project onto a wall, no need for a table since we're using tokens in Roll20, with good lighting for main rooms and a conference room where we can adjust the lights to be darker at the wall where I'm projecting. I've been using an Epson 1761W with 2600 Lumens. https://www.amazon.com/Epson-PowerLite-Brightness-Lightweight-Projector/dp/B0085ZJTAE


If I were running games only at my house, which I seem to only do on rare occasions anymore, I would love to be able to put a LED flat screen TV on a table or build one into a table. Using a TV probably would give the best colors, but may not be the most convenient due to heat and spilling drinks issues, plus the space it would take up.

This should work:

https://www.amazon.com/Microsoft-Surface-Tablet-10-8-inch-Professional/dp/B071WV2L4Q/ref=sr_1_3?s=pc&ie=UTF8&qid=1501134498&sr=1-3&keywords=Surface+3

The keyboard is sold separately but you can get an inexpensive bluetooth one.

here we go