It's a longstanding issue with giving players weapons in Source/gmod. When you're in a cramped location, the engine can decide the weapon can't be spawned because it doesn't "fit" (even though a player fits perfectly well there, it's bullshit). TTT tries to use a fallback method if it detects this, but I have no idea if that works. If you find it happening in specific reproducible spots, I can test things and possibly fix it.
So just don't buy weapons in small areas?