For us, what's been working is to offer around 2 hours after she last peed or pooped. Since she's consistent about telling us when she needs to poop, I don't worry about that (well, if she farts a lot, I'll ask, and generally get a toilet-sign and her heading to the bathroom

), but she doesn't seem to know about pee yet.
If I suggest it in between times, .e.g waking up from a nap or in the morning or before I go to bed (she sleeps through that last one), I won't insist on her trying. If it's the two hour mark, I do try out different things to get her to sit. Such as giving her a glass of water and sitting her on the potty on the couch (her new thing is liking height

) Generally if she does have to pee at all that distracts her into just going, and if she really doesn't need to she tells me off in baby-jargon.
Oh, and she's pretty much bare bummed or in undies unless we're going out, didn't think of mentioning that because it's been that way for a good while now.
What you do really is going to depend on how you feel about puddles vs laundry and how warm your house is and how cold your ds gets. I'd definitely figure out a pull on/off style diaper (e.g. fasten his current diapers looser) at a minimum. Some people use trainers until 1-3 have gotten wet, some people do bare bummed time for a set period.
Lots of things to try, and they'll all end up working and won't hurt your LO. If you feel silly having him in a dry diaper all day, use trainers more, if you feel frustrated at mopping up a puddle, use diapers more, like that.