I've been focused on TOS, TNG, ENT; and I've lost touch with some of the streaming shows, though I did get to see all of Picard and Prodigy. I'm kind of wanting to go back to the 2009 reboot film and watch everything from that forward in release order, but then... does it matter? This is what I was able to come up with from Wikipedia.
Star Trek (reboot trilogy)
Star Trek (2009) / Into Darkness (part 2) / Beyond (part 3)
Star Trek (streaming era)
2017: Discovery (S1)
2018: Short Treks (S1)
2019: Discovery (S2) / Short Treks (S2)
2020: Picard (S1) / Lower Decks (S1) / Discovery (S3)
2021: Lower Decks (S2) / Prodigy (S1-P1) / Discovery (S4)
2022: Picard (S2) / Strange New Worlds (S1) / Lower Decks (S3) / Prodigy (S1-P2)
2023: Picard (S3) / Strange New Worlds (S2) / Lower Decks (S4) / Very Short Treks
2024: Discovery (S5) / Prodigy (S2) / Lower Decks (S5)
Am I overthinking this?
I like watching things in release order when it's first time or mostly forgotten, but sometimes, that can get carried away.
I know the Shorts follow up Disco S1 and S2, and SNW follows Disco S2. Is anything else interconnected? Is the above watchlist just too much work?
I am looking for serious answers. 
Star Trek (reboot trilogy)
Star Trek (2009) / Into Darkness (part 2) / Beyond (part 3)
Star Trek (streaming era)
2017: Discovery (S1)
2018: Short Treks (S1)
2019: Discovery (S2) / Short Treks (S2)
2020: Picard (S1) / Lower Decks (S1) / Discovery (S3)
2021: Lower Decks (S2) / Prodigy (S1-P1) / Discovery (S4)
2022: Picard (S2) / Strange New Worlds (S1) / Lower Decks (S3) / Prodigy (S1-P2)
2023: Picard (S3) / Strange New Worlds (S2) / Lower Decks (S4) / Very Short Treks
2024: Discovery (S5) / Prodigy (S2) / Lower Decks (S5)
Am I overthinking this?



