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My daycare provider suggested this process and it worked well for us and maybe will work for you too.  (Consistency was more important than the age as a 21 month old boy did this at the same time as my son who was 29 months) 

First get prepared. Big boy pants, pull ups, reading material (short, small books worked great) stickers or tattoos for rewards a 60 minute timer w/ bell.   

Week 1:  put him in pull-ups: set the timer for every 20 minutes, when it goes off, take him and have him sit (backwards - facing the tank) and reward him just for sitting on the potty with a sticker. (we had a paper on the fridge that he could put them on afterward).

Week 2: put him in pull-ups with big boy pants on the outside. Set the timer for every 40 minutes (go to 20 or 30 if he's wet by 40) and same routine. This week I gave my son a sticker just for sitting and a Thomas tattoo for going.

Week 3: big boy pants on the inside - pull-ups on the outside. If he's doing well with the 40 minutes dry then move to sitting on the potty during transition times ie... out of bed, after breakfast, before going somewhere etc... also have daddy take him in to the potty with him.  For the younger boy at daycare it was thrilling for him to be doing the same thing the older boys were.  So some friendly male competition helped the process along.

By week 3, my son was dry all day, naps and night time with a few exceptions. But this was just the process that worked well for us. Definitely a time commitment that not everyone has.  Luckily for me, I have a fantastic, dedicated daycare provider. As you can imagine everyone who cares for your boy during this time has to be on board for it to be successful.   God Bless and Good Luck!

Is he generally dry through the night?

How long is he able to hold up between diapers?

It doesn't hurt to try.  For my son I went to pampers.com and got their potty training chart.  For every step of the process we would put stickers on it to make a game out of it and make sure we didn't miss any steps.  And yes I gave him a treat if he went on the potty when we were done.  If he doesn't indicate any interest in training just leave off for a couple of months and try again.  As kindergarten is your end goal date you have three years to actually get the process down, just try not to get frustrated and rush him.