How to know when its too much?? GUYS help mostly...?

ive been textin a guy for awhile and weve become pretty good friends. hes not in school (tho hes 16, moved) and i am but sometimes he'll send me good mornin messages even tho i wont reply till after school haha :) and we text like every day, even sometimes late at night, depending on if we talked already or not. usually i text him (idk why but i usually do) becuz he wont text me if i dont hah he said he loves talking to me and that im cool to talk to but he doesn't make the move to talk to me first....? doesnt make sense to me but watever. anyways, my question: when is my textin him too much or overbearing...? i dont want to be the one to always text him becuz idk wat hes doin and he usually says hes jamming or goin to the skatepark but when i dont ask him, who knows wat he could be doin. maybe hangin with him family at dinner or sometimg. that kinda thing i dont want to interrupt. so how can i know when i should leave him alone? every time i text him, he always texts back hi with a smiley face so i know he doesn't mind me textin or is glad i did but where should i put the line of overtexting...? HELP! i dont want him to get annoyed of me.... :/