All this here will be my own personal opinion.

So, firstoff, please, don't ever excuse anything with "it's from a place of insecurity". It may be true but the person with the insecurity DOES have a RESPONSIBILITY to sort it out. Responsibility like.... Go to therapy, or find whatever other kind of support and help with sorting it out before it ruins their own lives and other people's lives too. If he will NOT own up to this responsibility, get out ASAP.

The rest will be strictly in mind with him having owned up to the responsibility and actually working on his insecurity. He does have more than the 'necessary little spice' of jealousy. He has to work on that, on his default mistrust with it.

So, for a few of the requirements you've listed, you need to decide if you are OK and if you agree with them. If not, then don't give in to his requirements. He seems to have very particular preferences, requirements and ideas, but if they are non-negotiable and are a deal-breaker for him, so be it. If you are not comfortable with them, then that'll just be the end of the relationship.

He basically has a right to having his own vision of a relationship about what he prefers, wants or needs and what he finds appropriate etc. You don't have to agree with that vision. You also have the right to your own vision of one.

So I would not want to outright declare him as manipulative or controlling, that was not unambiguous enough for me from what you've posted.

He clearly has these set ideas about what's appropriate. He additionally sounds very conservative. These ideas and conservativeness are not necessarily out of some evil manipulative or controlling or abusive intent however. It could still be that he's manipulative and selfish, of course.

If he's upfront about his requirements and preferences and is willing to either negotiate or let you go without blackmail if you don't agree with them, then I would not say he's either manipulative or controlling. If he will not let you disagree and/or will try to not let you go, then he is and then I would say RUN far and fast!

And if you feel like, he's too pressuring, and you just don't feel like you can work with that, that's still not necessarily him being a manipulative controlling person, it could be you two just do not work together (re: your thread's title). But if there are those red flags about actual manipulation and selfishness, then it's not okay, of course.

One more thing. Does he also have ideas on what he should do so you feel secure in this relationship? Or is it all about what you should do so he feels secure? Try to evaluate this and the rest as objectively as possible.

I'm not sure if I understand this one. Was the idea you like to go clubbing on your own and he likes to travel alone so you both do these hobbies? But you cannot travel alone? I agree that's unfair and it's a too rigid and mistrustful way of doing a relationship.

It's where your giving in would end up him being too controlling even if he was originally not controlling. It would mean you give him too much space controlling things at your detriment. He really should relax there and allow for fairness and basic trust, even if he's some kind of a conservative guy.

Some of the other requirements didn't make me concerned too much (unless I missed or misread something), as it's mostly up to mutual and respectful agreement about preferences, except this one as this is clearly an unfair arrangement unless I misunderstood.

I would say this however sounds a bit naive. If you were to believe such a naive view on unconditionally trusting people and ignoring red flags, you will likely end up feeling betrayed.

Most people are not saints with perfect self-control that can just magically ALWAYS keep from giving into unwanted impulses, so they will naturally make some mistakes, and so maintaining appropriate and decent habits and a sensible way of living are important. Much like keeping a good, healthy diet. In line with that, you can and should trust your partner but if you see red flags, you cannot continue trusting blindly.

So like I can understand him being bothered by you accepting drinks in bars from male strangers. I'm not even a guy but I can understand that one. If you accept these drinks it could be that they put something in your drink or just plain have you drink too much and then get you into bed even if you never wanted to cheat on your partner. This may not bother every guy, but some guys just won't like this possibility and may feel protective of you, as well.

But you previously willing to accept drinks like that, it would not mean that you are someone not trustable. You may only seem that way to some boyfriends if you insist that you still want to regularly have drinks with random guys in bars. Even if you have the best intentions and not ever have the intent to cheat. That would definitely make you seem as too loose to some men even if you are not that type of person. They just will not be able to really discern if you are not that person.

Your boyfriend may also not be able to discern it and so may want to insist on these safe habits and ways of living. And similarly, he may not be able to realise that doing it maybe once a year is not the same as doing it regularly like every weekend night. Some are just that rigid, especially at his age. I don't know if he's like totally rigid on it or is okay with it if it happens infrequently, or even VERY infrequently (comes down to his personal preferences and views and capabilities at that point and those being in line with your own vision of things or not).

All in all, some guys just won't like it. But not all guys will have an issue with it. Much like, some women won't mind such a "rule" or expectation, and some will mind. And it does not necessarily have anything to do with actual trustworthiness. So again, if you find him too strict on this one, then you don't have to be with him.

The same kind of reasoning applies to staying with those male flatmates at your friend's place. It in part again comes down to personal preferences and in part it could be an actual risk, depending on the circumstances, even if you have zero intention to cheat.

EDIT: The part on him coming too that seems unnecessarily protective and/or mistrustful for sure. You are not some kid needing to be escorted to a foreign country.... if I were you I would insist on not doing it that way. Though if he otherwise turns out to be a decent and responsible guy - including taking responsibility for his insecurities - I would also try to understand his feelings on it.

Hope some of this helped. Try to have nuanced judgment on the situation. Do not ignore red flags, your gut feelings on what may be wrong, but do not judge him too fast either in some black and white way. And last but not least, if he doesn't want to work on his insecurities or hear you out on how it's unfair if he gets to have bigger requirements than you, then do run!! As all that would be major red flags.