I'd skip the gift. If it takes so much thought to decide if one is appropriate, it probably isn't. Kind of like sex.
The reason it sounds like it matters to you so much, I'm guessing, is that gifts are your LL. I'm a gifts person myself. It isn't about materialism, it is about the genuine thoughtful caring, understanding, and insight into the other person that a good gifts demonstrates that is important. I'm sure it is as hard or harder for you NOT to give a gift than it is for you to refrain from saying ILY over and over again.
Anyway, at the very least, a gift from you is a sign of intimacy. Don't mistake that. And, you know that something silly and homemade is even moreso...
I'm writing really to respond to this question:
Since he knows I have no kids, knows his mom's BBQ plans - do I wait to see if he suggests anything? I doubt he will, though.
YES. By all means WAIT. Give him the space to figure out what he wants and ask for it. If you are right that he suggests nothing, that is all the more reason NOT to have inserted yourself into his plans.
I think he might surprise you, maybe not this time, but if you keep giving him space he might just figure out that HE would LIKE to make plans with you. As long as you keep doing this for him, he won't have any idea that is the case. What will stick in his mind is what a hassle it is to turn you down when he doesn't want to see you.
