A:AnswerYes but as with any Apple laptop you will need an adapter. Anker makes a quality hub with HDMI on it for around $40. The apple AV adapter is overpriced.
A:AnswerModel A2338
Any MacBook Pro 13” 2016-2020 case should work. Only things to look out for, depending on the case - this model only has USB-C ports on one side and be sure to get a case that’s Touch Bar friendly if it wraps around the keyboard area.
A:AnswerNot sure about the software upgrades but the machine only has 2 USB-c ports. My wife found a doggie online that plugs in to both ports and has all the other ports available including an HDMI. Hope this helps.