Improve schedule and mackup reliability

- bin/ssr-schedule: use `launchctl bootstrap`/`bootout` (modern API) with
  legacy `load -w` fallback. The previous `load -w`-only flow silently
  no-op'd on macOS 10.15+ in some configurations, leaving `ssr status`
  reporting `inactive` after a successful `ssr schedule on`.
- bin/ssr-status: query the service via `launchctl print`/`list <label>`
  for consistent active/inactive detection.
- lib/mackup.sh: pre-materialize iCloud placeholders via `brctl download`
  and retry `mackup -f backup` up to three times to dodge the recurring
  `OSError [Errno 66] Directory not empty` race between mackup's rmtree
  and iCloud's filesystem provider. Soft-fails so the rest of `ssr sync`
  still runs even if mackup never settles; logs actionable hints.

Co-authored-by: Cursor <cursoragent@cursor.com>

lib/mackup.sh

@@ -32,9 +32,63 @@ ssr::mackup::configure() {
     ssr::ok "Wrote $cfg"
 }
 
+# Force iCloud Drive to materialize placeholder (.icloud) files under the
+# Mackup storage directory before mackup walks them. The most common ssr sync
+# crash is `OSError [Errno 66] Directory not empty` raised by shutil.rmtree
+# inside mackup when iCloud lazily re-creates dataless placeholders between
+# listdir() and rmdir(). Pre-downloading sidesteps the race.
+ssr::mackup::_materialize_icloud() {
+    local mackup_root="$1"
+    [[ -d "$mackup_root" ]] || return 0
+    case "$mackup_root" in
+        *Mobile\ Documents*) ;;            # only worth doing for iCloud
+        *) return 0 ;;
+    esac
+    # `brctl download` is the documented way to request file materialization.
+    # Available on macOS 10.12+; silently skip if missing on older systems.
+    if command -v brctl >/dev/null 2>&1; then
+        brctl download "$mackup_root" >/dev/null 2>&1 || true
+    fi
+    # Belt-and-braces: prune any stub files that survived the download
+    # request (sometimes left over from interrupted prior runs).
+    find "$mackup_root" -name '*.icloud' -type f -delete 2>/dev/null || true
+}
+
+# Try `mackup -f backup` with a small retry budget. iCloud-induced races are
+# transient: a 2-second sleep is usually enough for the provider to settle.
+# We deliberately do NOT abort `ssr sync` on persistent failure — the user
+# still benefits from brew dump, cleanup, and the unmanaged-apps scan that
+# run afterwards. The failure is surfaced loudly via ssr::warn and syslog.
 ssr::mackup::backup() {
     ssr::log "mackup backup"
-    mackup -f backup
+
+    # Derive mackup root from ~/.mackup.cfg (path + directory).
+    local cfg="$HOME/.mackup.cfg" mackup_root="" path dir
+    if [[ -f "$cfg" ]]; then
+        path="$(awk -F= '/^path/{gsub(/^[[:space:]]+|[[:space:]]+$/,"",$2); print $2}' "$cfg")"
+        dir="$( awk -F= '/^directory/{gsub(/^[[:space:]]+|[[:space:]]+$/,"",$2); print $2}' "$cfg")"
+        [[ -n "$path" && -n "$dir" ]] && mackup_root="$path/$dir"
+    fi
+    [[ -n "$mackup_root" ]] && ssr::mackup::_materialize_icloud "$mackup_root"
+
+    local attempt rc=0
+    for attempt in 1 2 3; do
+        if mackup -f backup; then
+            return 0
+        fi
+        rc=$?
+        ssr::warn "mackup backup failed (attempt $attempt/3, rc=$rc)"
+        if [[ $attempt -lt 3 ]]; then
+            [[ -n "$mackup_root" ]] && ssr::mackup::_materialize_icloud "$mackup_root"
+            sleep 2
+        fi
+    done
+
+    ssr::warn "mackup backup did not complete after 3 attempts (rc=$rc)."
+    ssr::warn "Sync will continue without it; rerun 'mackup -f backup' manually,"
+    ssr::warn "or switch ~/.mackup.cfg to a non-iCloud storage path if this persists."
+    ssr::syslog "mackup backup failed after retries (rc=$rc)"
+    return 0   # soft-fail so the rest of ssr sync still runs
 }
 
 ssr::mackup::restore() {