Hi WTBH,
I have to say I'm a bit with redatlanta on this one. I don't see red flags here. I'm not saying his way of phrasing things shouldn't have been a trigger for you or that it shouldn't have offended you. But I don't think it automaticaly means that he's controlling and manipulative.
It is unfortunately is a fairly normal way of speaking. People often say things like that, especially your first red flag: "I know this person had x, y, z ulterior motive for asking me to do x, y, z". I can't say exactly what he meant by "I know", but to me it reads as "he feels he knows ..."
In general, the use of the "I" statements, and say things like "I feel" are communication tools that people lean in therapy. I've also read somewhere that using "I feel" phrases when stating an opinion is something that women tend to do naturally, and men don't. It's cultural conditionning and what we've been brought up to do.
IMO, the red flag would be if you calmly explained to your gentleman what hurt you in his statements and he kept doing it anyway. He was appologized, it is now up to you to decide what you are going to do about it. But I think it is also your job to tell him what has hurt you and why. He can't know what hurts you if you don't tell him.
Even when they have the best of intentions, people still hurt people without setting out to do so. It think it's once we've told someone about our triggers and they keep pushing those buttons that we can say that they are intentionally hurting us. It becomes a question of trust. Do you trust your gentleman (and yourself) enough to be honest and tell him what has hurt you and why, and trust that once he know, he will do is best not to do it again? You also have to keep in mind that even by telling him, and even is he really has no intention of hurting you again, he might not be successful 100% of the time. We are all human after all. I don't think anybody here can say that they are perfect all the time and that they don't revert to old habits from time to time. It doesn't make us bad people, just human.