All good advises but there is, I feel, one thing missing and since it's a core concept of D&DN, that's odd: Advantages & Disadvantages, though the API thing just prints out double rolls. This post will probably be too late but heh, who knows... I'll therefore just give my 2 cents, based mostly for a 100% chat based game, in which the nice API thing is a bit too spammy and mechanical. You'll find the sheet Attribute structure that I use for PCs and NPCs at the bottom of the post (basically made a template, then I just Duplicate) Here's an example macro for a STR check /ooc STRENGTH CHECK - [[?{number of dice|1}d20?{drop or keep} + @{STR} + @{PROF} + ?{other bonus|0}]] Or an INT check /ooc INTELLIGENCE CHECK - [[?{number of dice|1}d20?{drop or keep} + @{DEX} + ?{other bonus|0}]] And a 1hd standard attack /em ?{Attack emote|attacks!} (ATK: [[?{Attack dice number|1}d20?{drop or keep}+@{TOHIT}+?{other hit bonus|0}]] / DMG: [[@{DAMAGE}+?{other damage bonus|0}]]) Or a Grapple check /em ?{description|tries grapples his target!} ([[?{number of dice|1}d?{dice type|20}?{drop or keep} + @{STR} + ?{other bonus|0}]] vs STR/DEX) I play 100% chat based games so the "input" system allows me to customize each actions quickly. These macros also allow for advantage/disadvantage on the go. By default, it'll be a normal roll, but you can use the same one should there be advantage or disadvantage, which to me is key for D&DN. Lastly, the "other bonus" is also key. By default it's 0 of course, but you never know what can happen and to keep the macro useful, having such input allows to apply the modifiers on the fly. These macros work with bless, bard songs and other effects because of these custom fields... As a GM, I also use things like this: For attacks without requiring a hit, causing damage with a DC /emas @{selected|token_name} ?{Attack emote|attacks!} (DMG: [[?{damage|d6}]], ?{save|STR} SAVE vs ?{DC|12}) For attacks just causing effect, with a DC /emas @{selected|token_name} ?{Attack emote|attacks!} (?{save|STR} SAVE vs ?{DC|12}) For attacks requiring a hit, causing damage with a DC /emas @{selected|token_name} ?{Attack emote|attacks!} (ATK: [[?{Attack dice number|1}d20?{drop or keep}+?{to hit bonus|0}]] / DMG: [[?{damage|d6}]], ?{save|STR} SAVE vs ?{DC|12}) You get the idea. And finally, a simple INIT tracker macro that allows to just select any token, add to tracker and repeat. /w gm @{selected|token_name} - initiative roll [[1d20 + @{selected|INITIATIVE} &{tracker}]] For the sheet, I use the first columns for the modifiers (simply easier to use in macros) and only keep the actual score (or max values) in the second column. The TOHIT and DAMAGE portions are the basic stats for melee and ranged attacks of course and INITIATIVE is used for just that. All PCs and NPCs are using this exact template, therefore all macros work on everything, with just a couple of personal macros added, mostly for PCs actions (as they decide to add things, spells, emotes, etc) and very specific attacks for NPCs. All in all, here are a couple of tips: Setting up your game structure BEFORE anyone actually starts playing (or you yourself start creating and adding too much stuff in there) is paramount I think. You NEED to think how you want to organize things, before you start actually making maps, tokens and whatnot, especially if you're going for a long campaign, where early mistakes will echo and add up the longer you go. Keeping ALL your base tokens, as you link them to sheets, on a separate map page dedicated just for that, is, I think, very important. Only link tokens from this page, then never just "copy/paste" tokens around but instead "drag/drop" from the sheets themselves, therefore making sure that you use the base token structure, not any altered one from a previous play map. This will keep your base settings constant AND you will always be able to go back to the original token should any modification is required. This is especially true for PCs, since they are the most likely to receive changes on the tokens in play as you go (light variation, effects, etc). Make your macros as generic as you can. There is just not enough space to keep dozens and dozens of macro to answer for every situation, so you just need a few, that can handle any variation of the theme. The last thing you want is to have superb macros for specific things, only to realize that they're completely useless in a situation because of a special modifier, event and whatnot, forcing you to manually type EVERYTHING.