Matt,
Your post is full of valid questions. However, consider the type of music you will be playing. I would consider a maple shell kit with a 45 degree bearing edge for projection. As far as quality goes, vintage drum quality is subjective. Some think Rogers are better than Slingerland, or Gretsch were the best during the 60's.....it's subjective. If you go vintage, the condition of the drums is what to focus on, make sure they are in good condition. A bad spot on a bearing edge can ruin the sound. New/Modern drums like the Catalina's you mention will sound a lot different. I can play my 59 Slingerland's, then step over to the PDP kit and hear differences in tone and sound between the woods and bearing edges.
Don't forget the hardware! Vintage hardware can't hold a candle to modern advances in the hardware of today. For that reason, if you are playing them out, you'll want reliability. Nothing worse than a pedal spring breaking, or a wing nut loosening during a 45 minute set(ask me how I know!).
PDP's Concept Maple's are quite affordable and quality you can see and hear in the drums and hardware.
If it's vintage you want, the floor is open to options. 70's Ludwigs are a good choice, Gretsch, Slingerland's........
Good Luck and the fun part is looking!D' Drummer