Okay to keep (infrequently) reaching out as long as he keeps responding?

Matched with a guy on an app about 6 weeks ago. Tons in common. Similar interests, hobbies, goals, values, etc. Could talk/text for hours with ease. Met up twice with him. Kinda awkward at first, but I had a really nice time once we both warmed up. I can tell we're both introverts and a bit shy.

Anyways... had a very heartfelt convo with him. He's still healing from his divorce 5 years ago and a broken engagement 1.5 years ago. I can tell when the 'not ready to date' is a polite rejection, but I genuinely don't think that was the case here. He deleted his profile on the app, and the way he spoke about his past relationships tells me he still has some work to do.

I've got my own shit to work on regarding self-esteem and anxiety. Both agreed that dating is off the table. However, he seemed very keen/up for hanging out occasionally. He also made one or two suggestive jokes, and I wouldn't be opposed to hooking up either.

tl;dr - The problem is I've reached out twice, saying I'm free if you're down for XYZ. Both times he gave an enthusiastic reply like "Okay, sounds good!" and then no follow-up. Guess my question is, when do I stop reaching out? If he didn't respond, I wouldn't reach out again. I also know he's kinda dealing with a lot of shit with work and life, so I'd like to keep letting him know I'm around. Just don't wanna keep annoying him.

Any advice? Maybe just casually reach out once a month or so over the summer?