Decision Matrix

At a glance

flowchart TD
    Start[New stack pick?] --> CLI{AI coding CLI}
    CLI -->|primary| Claude[Claude Code]
    CLI -->|fallback / spot| GemCodex[Gemini or Codex CLI]
    CLI -->|wrapper| Reject1[Avoid until 2027+]

    Start --> Mux{Terminal mux}
    Mux -->|fresh start| Zellij[Zellij]
    Mux -->|existing muscle memory| Tmux[tmux]

    Start --> Net{Cross-device}
    Net -->|default| Tail[Tailscale + SSH alias]
    Net -->|public SSH| Reject2[Avoid: brute-force surface]

    Start --> KB{Knowledge mgmt}
    KB -->|markdown-first| Obsidian[Obsidian]
    KB -->|server-locked| Reject3[Avoid: poor agent fit]

AI Coding CLI

Option	Pick	Reasoning
Claude Code	✅ primary	Best agentic execution I’ve used; Anthropic’s Opus/Sonnet tiers have real headroom; the $100/mo Max plan makes intensive use affordable
Gemini CLI	◐ fallback	Free tier; different model family for sanity checks; spot tasks when rate-limited on Claude
Codex CLI	◐ alternative	OpenAI ecosystem fluency; second option for comparison
OpenCode / OpenClaw / T3Code	❌ avoid	Ban risk, ecosystem instability, unvetted security surface
IDE-embedded (Cursor, Continue, Cline)	❌ for primary use	Couples AI to editor; bad for cross-device portability

When to revisit wrappers: 2+ years clean operation, verified code audit, provider cooperation. Maybe 2027.

Terminal Multiplexer

Option	Pick	Reasoning
Zellij	✅ primary	Discoverable keybindings (status bar), modern Rust impl, works well with Claude Code + OpenCode
tmux	◐ fallback	Universally installed, battle-tested; some tools (OpenCode) historically quirky inside tmux
WezTerm mux	❌ for sessions	Local-only; doesn’t cross devices. Fine as terminal emulator though
screen	❌	Older than tmux; no reason to pick it today

Cross-Device Access

Option	Pick	Reasoning
Tailscale + SSH config alias	✅ primary	Device-mesh auth; no public ports; MagicDNS gives stable names; Tailscale SSH removes key management
Termux (Android)	✅ for phone	Real Linux userspace; full SSH + tooling
Termix (iOS)	◐ if needed	Less powerful; no Linux userspace; workable for emergencies
GitHub Codespaces	◐ for specific cases	Different model; fine for cloud-first devs, not for my-own-machine workflow
Raw SSH over public internet	❌	Public exposure; brute-force surface; key management tax
Headscale (self-hosted)	❌ for now	Control-plane maintenance tax; free Tailscale fits my use

Knowledge Management

Option	Pick	Reasoning
Obsidian	✅ primary	Plain markdown on filesystem; strong plugin ecosystem; now has CLI; my Obsidian-Flavored-Markdown works with this site
Obsidian CLI (v1.12.4+)	✅ for automation	Search/open/get from terminal
Logseq	❌ for me	Outliner-first UX; prefer document-first
Notion	❌	Not plain text; server-locked; poor agent fit
Roam / similar	❌	Same concerns as Notion
Plain markdown + VS Code	❌	No graph navigation; drops once vault gets large

Image Paste for Terminal AI

Option	Pick	Reasoning
Zipline (self-hosted) + ShareX + sharex-clip2path	✅ primary	One-hotkey screenshot → URL; Tailscale-gated; zero public exposure
Imgur / public paste services	❌	Public exposure; privacy concerns for work content
Terminal-native image display (iTerm2’s imgcat)	◐ for some cases	Doesn’t give AI an accessible URL

OS / Runtime

Option	Pick	Reasoning
WSL2 on Windows	✅ my choice	Windows is my primary OS; WSL2 gives Linux for dev tools; best of both
Native Linux	✅ equally good	What most dev machines run; everything in this scaffold works natively
Native macOS	✅ equally good	Similar — most tools work identically
Windows without WSL	❌	Most dev tooling assumes Unix; friction is constant

Editor (alongside terminal)

Option	Pick	Reasoning
VS Code	✅ primary	Good extension ecosystem; works well alongside terminal CLI
vscode-terminal-workspaces	✅ my ext	Sidebar GUI for tmux-style sessions (works well with Claude Code, Gemini CLI)
vscode-terminal-image-paste	✅ my ext	Paste clipboard images directly into terminal (alternative to Zipline flow)
Neovim / Helix	◐ for some	Terminal-native; good if you prefer terminal everywhere

Home Lab

Option	Pick	Reasoning
TrueNAS (specifics in 03-work/homelab/)	✅	ZFS, containers, decent UI
Self-host behind Tailscale	✅	Auth via device identity; no public exposure
Public-facing with reverse proxy + auth	❌ for most	Adds config surface I don’t need

The general rules

1. Pick one primary, have 1–2 fallbacks. More than three options per layer is indecision.
2. Prefer official over wrappers until wrappers prove 2+ years of stability.
3. Tailscale-gate anything self-hosted unless there’s a specific reason to expose it.
4. Terminal-first, editor-integrated. Editors sit alongside; terminal is the universal substrate.
5. Revisit every 6–12 months. The ecosystem moves; old decisions expire.