This may sound dumb but don’t just think of price and quality, try to buy as near to new as you can.
For example, the 2019 MacBook Pro architecture is brand new from the 2018.
This architecture won’t change until the G5 revolution. Ports are the fastest/best available now, but over the next 5 years they will make way for the newest best thing. If you buy a monitor that requires adaptation of any kind (software or hardware), in a couple years you may need a second adaptation or even not be able to use it at all. Also, each hard connection is one more chance for a corruption to occur, so generally avoiding any connectivity issues is a good rule.
For example if you upgrade your cpu or new software requires higher data transfer rates. Equally bad (or maybe even worse), loss of data may be minimal and unnoticeable in use but cause data loss at press because any number of the profiles is going through too many iterations and breaking down the quality.