I'm about to take my first steps into the VR world having tried my friends Q1 ages ago and have always wanted one since.
I didn't want to drop £400 on the original Q1, but I can get the Q2 for £270 new, which I'm happy to spend (although after all the accessories it'll be close to £400!)
Also will be buying the GOMRVR Halo strap and a cheap £10 PU leather face cover to use whilst I wait for the VR Cover Facial Interface to be back in stock and then I can buy that with the controller grips.
I've had a look at games, and I'm going to have to limit myself on buying initially as there's so many that look good!
Are people buying on Steam and then using VD or just buying via the Quest store? As the games through Steam are cheaper when on sale, but then I guess the games aren't portable and it's still an extra step to do before playing.
I think initially I'll pick up the New Year's Pack (Gun Club, In Death: Unchained, Space Pirate Trainer), Beat Saber, possibly Vader Immortal Episode 1 and Superhot.
How often do games go on sale? If it's anywhere half as regular as Steam sales, I'll be happy to wait as and when they drop in price.
It's great, enjoy...I also have the GOMRVR en route

It is hard where to focus (games wise), like you said, a discounted bundle is a good start to get you going. I'd wait for sales on Beat Sabre as it's quite expensive (but it's up to you of course) - I can also recommend Eleven which is table tennis game/sim.
Be careful, on the store there's a table for each type or game (ie if it plays via PC or headset) - not all games are cross-buy, but there is a way to search for cross-buy titles...my advice, buy games that require minimal lag for the headset so you don't have the lag from the PC - also these games can be taken anywhere so a great reason to buy those. Eleven and Beat Sabre are good examples.
Don't know enough about sales - they don't seem great, just keep an eye on store, there's usually a daily deal...I did a similar thing to you, bought a few to get me going and now waiting for sales to pick up games that interest me. Oh, and Saints and sinners is apparently an awesome game.