What brand should you start with when it comes to vintage?

Go take a look at Second Time Around Watch - They are (relatively) reasonably priced, knowledgeable, and nice. I have not bought from them but have visited and it would be a good place for you to get a feel for the vintage market in your area.

There are other shops like Wanna Buy A Watch / Craft & Tailored, but they seem to cater to more high end clients, so maybe not the best place for a beginner.

Seiko. The amount of incredible vintage options for rather cheap is incomparable.

American made vintage watches can be a good starting point.

Here is a site to start at. https://www.vintagehamilton.com/

EDIT: Check out the “GRANDPA'S WATCHES FOR SALE” section for brands other than Hamilton.

Check out https://vintagewatchservices.eu/. Stian buys vintage watches on eBay, then makes videos of his work on YouTube restoring the watch. His work is excellent and you can be sure any watch you buy from him has been restored to engineering spec.

Have a look at Universal Geneve. Not just the Polerouter , which are decent quality, lots of spares available if you have issues. Very cheap way to get a micro rotor watch.

Ask @hamblar on Instagram (he literally runs the the website for the Polerouter)

There are many other manually wound watches with high quality movements too.

Go with Seiko, then check out Omega I'd say. Whatever you do buy the seller, not just the watch as they say in vintage circles.

I say Longines, Omega and Certina. 3 brands I find reliable.

I was about to suggest some basic Swiss jobbers like most of my vintage collection, until I saw your budget. Equal parts being broke and selfish have made me fairly well versed in affordable vintage watches. Here are some brands that are still well-priced for the most part and perhaps a little bit under budget.

Rado:

Great quality watches, with many featuring solid automatic movements (not sure whether they came with ETA or AS movements.) My favourite is the DiaStar, especially the gold-plated ones. They pack some serious tech too, with the case being made of a tungsten carbide alloy and the crystal being sapphire. You can find decently-kept examples for as little as a few hundred USD. Hope you like diamonds, because a lot of them feature the sparkly stuff.

Nivada Grenchen/Croton

If you like tool watches, Nivada Grenchen/Croton has a lot to offer. The Antarctic is a great watch with a lot of history and I am a proud owner of one. They feature a variety of ETA automatic movements, many of which nickel-plated for magnetic resistance. These are getting expensive though, but your budget should be able to get you a good example with change to spare.

Some more obvious (but oftentimes reliable and safe) choices include Longines, Omega and Tudor.

What I'd recommend though is to maybe start off with a cheaper watch like a Seiko (if you see the 80s as vintage, some quartz Credor models are still very good value) or perhaps some small, since defunct Swiss brands, which usually have decent movements and pretty good looks.

Some oddball picks, I know, but I hope this helps.

The key, I find, to vintage buying is having knowledge. You can never do too much research, especially if you want to drop a few thousand USD. I wish you all the best and hope that you find the vintage piece for you!

1967 Sportsmatic 6619-9000.

I’d say go with Omega. Gazillion models overs the decades. You can find good ones at any price. Check https://www.omegaenthusiastltd.com/omega