OK, as a bloke, this guy sounds utterly disgusting, and not someone I'd like as a friend, let alone as a romantic partner!
Going through your list (and yes I've ranked them in terms of how much of a red flag they are! I just wrote one as a 5/5 and then figured I'd go back and do the rest! Anything above a 3/5 is an instant dumping offence):
-made a few silly sexual jokes whilst messaging, before we met eg..I asked him if he played a musical instrument and he made a joke about wanking
2/5 - I've had girlfriends who enjoyed this sort of stuff, and some that didn't. He misjudged the line on this one. If he carried on after you told him to stop, then it's a 4/5
-first date in a coffee shop, I removed a long sleeved top as was too warm (had another top on underneath obvs) and he went "wahaaayyy" as if I was stripping
4/5 - God it's just so cringe
-made a joke about all women having a base level of psycho
5/5 - Nope, massive red flag. Hates women
-referred to disabled people as "Scopey"
5/5 - Another instant dump
-met a colleague of min at a works do and told me she was "rough" and this is why he doesn't date women from her area
5/5 - Judgey little prick
-despite the fact he is on amicable terms with his ex wife, told me laughingly, when she asked for a divorce, that he had called her a "fat old witch" and threatened to take her pension
4/5 - Not that he said it to his wife, but that he felt the need to tell you
-told me inappropriate details about his ex including that she was restricted in sexual positions she could do due to bad hip and that she could orgasm immediately from anal sex (he told me this whilst we were in bed by way of praising my comparative flexibility)
3/5 for the hip thing, rising to a 4 when he started banging on about anal, and then rising to a 5 because he told you about it in bed
-said "You look lovely in your dress; my ex wife never wore them because of her body type"
1/5 - This ones OK, it'd be a 0 except there was no real need to mention his wife
-met an acquaintance of mine and said "You're naturally beautiful, not like women like that who plaster on the make up"
2/5 - Again, on its own, not the end of the world, would just get a hard glare from me.
-when I was trying to encourage him to get o know me better and asked if there was anything he wanted to know about me (cause I had tried to ask him lots about himself) he said "What is the smallest penis out there have encountered?
3/5 - DP and I have actually discussed this. 5 years into our relationship! Is he really that short of conversation a few dates in?
-told me, in bed, that he had yet to encounter a smelly vagina
2/5 - He really doesn't have much between the ears does he?
-told me he had dumped a woman as her pubic hair was too long (after avoiding having sex with her for weeks)
2/5 - Look, individually some of these aren't the end of the world, but cumulatively they're really stacking up aren't they. He sure does love talking about his previous shags doesn't he!
-shortly after we began a sexual relationship, told me he thought genitals in general were gross and then was annoyed with me when I went a bit quiet and distant for a few minutes after he said that
2/5 - I struggled with this one. Multiple women have told me the same thing. Not generally when they're trying to woo me though
-first time we had sex, he seemed clueless despite being married before and many relationships. He kissed me for a while and I was expecting some foreplay (I know I could have initiated this but I had lead on taking him up to my bedroom and removing clothes so didn't want to lead ointment everything). Without so much as touching me intimately, he entered me without a condom. He stopped as soon as I told him to and was visibly upset and said he thought I had wanted it as we were naked and he was laying on top of me. He was genuinely upset and I ended up comforting him!
This one started at a 5/5, but given your update further in the thread I'm dropping to a 4. It sounds like there was some genuine confusion there
-I disclosed to him that I had been sexually assaulted in a previous relationship. Despite this, he sent me a GIF that appeared to be of a woman being assaulted, face down on the floor and crying..looked like really rough porn but you could only see her face.
Fucking hell, this one just breaks the scale. 5/5 for sending a woman he's dating porn. 50,000/5 for it being abuse porn. Infinity out of fucking 5 for sending that to a woman who'd disclosed her own assault.
-he had some very laddish mates and he said he didn't judge them for sleeping with prostitutes although it was not something he would do. Told me they had all been giggling in the pub about some story about a woman with a massive anus.
5/5 - You can't buy consent. He approves of it, even if he's not done it.
-in a weird coincidence, a mate of his turned up at my house to collect something I had listed on marketplace. He arrived 15 minutes earlier that agreed and ex and I were in bed. When ex realised who it was, he got dressed and said hi his mate. he later told me that the incident had been the subject of joking on their group WhatsApp, with one them writing "He was just pulling out of her as he arrived!"
The message itself, not his fault. The fact he needed to tell you about it. 4/5
There's about 4 things on that list that I wouldn't instantly dump someone for if they were a one off. But even two of those cumulatively would have chucked him straight in the bin.
And then there's the rest.
To be honest @RedflagGreenflag , this guy probably shouldn't have made it passed the messaging stage. Certainly not past the first date. It's great that you've dumped him, but you need to do some real work on why you thought any of these were worth putting up with.