The second version is better.
With the first version, you're exerting uneven pressure on the pins inside the connector, the ones closer to the end of the tool will be pressed a bit more. Also, when you squeeze the tool the metal "bars" that push those copper pins in the wires are ever so slightly pushed sideways, which can in some cases (low quality plastic) enlarge the channels where those pins reside inside the connector.
The second version is designed to push the metal bars straight down on the jack without uneven pressure or any other issues. It's also easier to use in some cases, if you don't have the strength to squeeze the tool you can use the side of the desk.
Years ago I've crimped about 200 cables for a small server room using two crimping tools (one of each kind), but the people who owned that building didn't do proper air conditioning and the room was hot and humid, at around 30-35c all the time. About 20% of the connectors made with the regular tool started to loosen up and had to be re-crimped after about 6-8 months, and only maybe 2-3% of the cables crimped with a tool similar to the 2nd picture failed. Anyway, can't say the tool is 100% responsible for this, because air conditioning was not the only thing they cheapened out, they bought cheap connectors as well.