Should I buy a 2019 Squire guitar or a early 2000's Squire guitar?

You're asking "should I buy a modern cheap copy or an old cheap copy?"

Buy a proper Fender.

Love how you ask "A or B" and get answers like "8". The classic vibes are exceptional values, great in their own right. Age not such a big thing as trying out and see which one speaks to you IMO

Why not spend a few more $ & get a proper Fender, or a few more than that & get a Gibson? Among other things, just the name on the head gives them a much higher resale value & makes them far easier to sell.

I'd go with the older one

I think you mean Squier.

Without knowing something about the actual guitars, their price and their condition and playability it's impossible to say. Try them both, consider value for money and buy the one you prefer.

Buy an American-made PRS instead.

2019. The new Squire's have better pick-ups and hardware than they used to.

maybe you can buy them both