What piece of software would you build and why?
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Paging Marco Arment! 
I’d build an amazing DAM – digital asset manager, with a bulletproof database, speed, and capacity for an enormous number of items/entries.
A clean, simple UI with customizable “looks” would be part of the design. Basically, a better Lightroom, shorn of the RAW developing part, and less prissy about embedding metadata in “original” files.
Why? I like keeping my (photography) assets, but new ways of finding them / looking at them, using embedded metadata combined with assigned metadata, would make sifting, evaluating and re-evaluating content so much less haphazard.
(Currently-available DAMs tend to fall down either on the question of scale, UI pleasantry and/or robustness.)
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I’d build the ultimate Personal Knowledge Manager, with all the great ideas of every app baked into one. EverRoamThinkKasten… 
Even though, to be fair, DEVONthink comes close.
I guess the true answer to that question would then be
I’d develop DEVONthink To Go 3 
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A proper spiritual successor to Starcraft.
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I would replace Tinderbox with something designed this century, that has all the features but an intuitive, responsive interface, supports export without having to learn HTML and arcane tricks, freely imports and exports data from multiple source (e.g., has a Share Extension – what a thought), and doesn’t crash at weird moments. I’d also provide documentation and tutorials that do not rely on volunteers. I would provide an iOS and iPad companion – maybe even with all the same features. And then I would make it open source, so that others could add plugins and integrations and make the Neo-Tinderbox grow into something really useful and awesome.
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From my line of work, what I sorely need is a cross-platform (macOS, iOS, Windows and … OK … perhaps Linux if it seems easy enough) literature reference manager app combining the best of citation managers (Bookends and ReadCube Papers) with the best of literature search engines (no-nonsense EZProxy direct tunneling + Google Scholar + …) with the best of annotation markup engines (PDFExpert) with the best / most innovative of annotation management tools (MarginNote and LiquidText) with the best search engine (DevonThink + GREP + complex query chains).
In any case, by the time I would consider the benefits of the first condition and the headaches to fulfill the question itself in the way that I’d really like to see it done, I’d realize that I would do better to pay someone to do it for me while I go skiing in the Alps.
So, I’d opt to pay handsomely to the developers of those other apps to make their apps talk directly to each other.
As a side benefit, I don’t really like the “everything and the kitchen sink” approach anyway.
–
JJW
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I would love this for my digital drawings. #featurerequest
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AugCog for knowledge workers:
Basically I just want my devices to realize when I’m going to totally waste my time for the next couple of hours before I’ve wasted my time for a couple of hours, and lock me out so that I go do something fun or relaxing instead. 
More seriously, systems that intelligently shape task, interface, and content to optimize for what I’m currently capable of and ready to do.
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I’d build a nice iOS and Mac tool to turn markdown into nicely paginated documents. (Something more user-friendly, flexible, and powerful that iA Writer templates or Ulysses export formats).
3D and VR, like an art gallery, so that you can build spatial memories of where things are. Punch a wall to add a doorway to another new room. Travel up, down, any direction.
Essentially, Manifold Garden, and you can hang pictures on the walls.
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Aha, sounds like you’ve watched Disclosure (1994) too many times! (Manifold Garden looks gorgeous, though…)
(I love that they design a VR database, and then the actual file retrieval is still just a filing cabinet.)
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Lol
Yeah, I forgot about that movie. Must - suspend - disbelief -
BumpTop is kinda sorta this way, but I think 2.5D. Haven’t tried it in a while.
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Remember when Apple Watch first came out and remote fart apps were immediately banned?
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Scrivener does this. It’s designed for rich text, but it does support Markdown. And it’s one-time purchase. And it’s got lots of export customization functionality.
That’s why I said Mac app.
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I have a Scrivener license for iOS. But it doesn’t like importing multimarkdown, and doesn’t seem to give me much in the way of export options.
I know the Mac version is more capable. But from looking at the forums, it still doesn’t give you the control or options you have in a word processor/pandoc/LaTeX. Many Scrivener users in the Scrivener forums mention having to do a fair amount of tweaking in something like Word after they compile/export in order to get the format they desire.
The app I really want would make it easy to create the styles/templates/etc. that would be used to turn your multimarkdown documents into finished paginated .pdfs (or properly styled .docx). Both iAWriter and Ulysses do this to a limited extent now, but they are HTML-based (rather than page-based) and so don’t give you much control.
My understanding is that LaTeX/Pandoc can do this. But there’s a very steep learning curve. I’d want some thing a bit more user friendly. (Maybe Affinity Publisher or InDesign would be able to handle this some day?)
User-friendly and flexible/powerful can only converge so much.
My wife and I have this dream (partly fleshed out last year when we had time on our hands) to build a game somewhat akin to Stardew Valley/Harvest Moon.
Mainly because I love programming, and she loves story writing, character design, and drawing; so, this could be a grand project together.
The list of programming techniques I’ll need to add to my limited repertoire is very, very long though!
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