- GUI vs. CLI Build command line tools first. Stick to the Unix philosophy of "Small is beautiful - do one thing and do it well" with each command program. Th

- GUI vs. CLI Build command line tools first. Stick to the Unix philosophy of "Small is beautiful - do one thing and do it well" with each command program. Then build a GUI app for whatever platform you want to support. Why CLI first? Command line tools can be used independently in scripts to automate various tasks (often repetitive tasks). This also further decouples programming logic so that you can work separately on the CLI code and the GUI code. (Here's some good tips on how to create a GUI for a command line tool - https://softwareengineering.stackexchange.com/a/204316 https://softwareengineering.stackexchange.com/a/204316 ). (Also keep in mind another Unix philosophy - "Reuse. Don't reinvent / rebuild". The GNU Coreutils command line programs that is available for multiple platforms can be a real asset for your project - https://opensource.com/article/18/4/gnu-core-utilities https://opensource.com/article/18/4/gnu-core-utilities . SQLite is another software that can really make your project simpler). - Language / UI Library Selection For creating the command line tools, I'd recommend whatever language you are comfortable with, but I'd opt for something that can create a standalone executable. For creating the GUI, consider the free and lesser known gem Lazarus https://www.lazarus-ide.org/ https://www.lazarus-ide.org/ - it can help you create native GUI for many platforms from one code-base (with some tweaks for each platform). A native GUI makes your application small, fast, and familiar to your users. The catch - you will have to learn Pascal to use it - if you are familiar with it, here's a good tutorial http://www.delphibasics.co.uk/Article.asp?Name=FirstPgm http://www.delphibasics.co.uk/Article.asp?Name=FirstPgm to help you get started. (Note: Lazarus is an open source fork of Delphi - https://www.embarcadero.com/products/delphi https://www.embarcadero.com/products/delphi ). Lazarus is better than QT because it uses the operating systems native GUI toolkit. You also don't have to worry about licensing issues with Lazarus and can even create commercial closed source applications with it for free. Lazarus is better than Electron because Electron bundles another layer over the OS (the chromium browser framework) to render the UI. That's a lot of additional software just for a GUI, and will make your software big (50+ MB) and slower (chromium is a resource hog). (But ... if time is a constraint or you don't have the inclination to learn yet another programming language, then go with what you are most familiar. If it is C++ choose QT. If it is HTML + CSS + JS, choose Electron.) - Use Cases I'd like it to be platform and filesystem agnostic - easily portable to another OS. Have fast indexing and search. Extensive tagging. (Using a database, like SQLite, can really help with all this).