I happen to be an expert on this topic!

You should watch the anime in the order it was released, with a single exception, Kizumonogatari:
- First season
- Bakemonogatari
- Kizumonogatari *
- Nisemonogatari
- Nekomonogatari (Black)
- Second Season
- Second Season
- Hanamonogatari **
- Final Season
- Tsukimonogatari
- Owarimonogatari I
- Koyomimonogatari ***
- Owarimonogatari II
- Zoku Owarimonogatari
- Off and Monster Season ****
Notes:
*The Kizumonogatari novel came right after Bake and is part of the same First Season, but it was adapted very late, around the time of Owarimonogatari I. Imo, it doesn't make much sense to watch it at that point, so just watch it in the season it belongs.
**Hanamonogatari is part of Second Season proper and was released right after Kabukimonogatari (Mayoi Jiangshi) in the novel, but it was adapted around a year after the Second Season anime ended. Because of how certain characters are developed in Second Season, it makes a lot of sense to watch Hana after Koimonogatari (Hitagi Love), but it's a choice you can make.
***The Koyomimonogatari novel was released before Owarimonogatari, but the last story from Koyomi connects directly to Mayoi Hell in Owari II, so it's nice to watch it right before it.
****The anime adaptation skips Orokamonogatari and Wazamonogatari from Off Season.
No need to overthink it. If you then want to read the novels, then just read them in the order they were released.