Is it better to paint wood siding or replace it with vinyl?
I  would recommend reading up on vinyl siding. It's really not as maintenance free as its manufacturers claim - it fades and becomes brittle. And unlike wood it can't really be repaired.

Not to mention it looks pretty ugly and fake.

Also if your house has any architectural details, then they would probably be covered up by the vinyl installation, significantly reducing curb appeal and possibly valuation of  your home