I want him to eventually be able to put him down drowsy but awake and for him to fall asleep himself. How do I go about doing this? Is it too late? Is now the best time to help him learn this?
The key - the single biggest factor in this - is that baby goes to sleep where they stay asleep. So don't move baby once asleep to somewhere else.
Tackling daytime naps, to avoid over-tiredness is the best place to start. Do you have a bouncy chair? If not, get one. Just a cheapy is fine, something you can sit and bounce with your foot while you're sitting on the sofa.
So - baby goes to sleep where he stays asleep - in bouncy chair. With dummy and naps are very, very frequent. The idea is to get as much sleep as possible so that by aged about 6-9 months you have good sleep routines in place ready to move to cot daytime naps.
Make daytime sleep as easy as possible.
A general guide is double the amount of awake time as sleep time, at a maximum. So if baby last had 40m sleep then awake time no more than 80m. It's likely that you might want to start the settling to sleep process at around 60m awake for example.
So baby wakes ~ note the time ~ then feed baby a new bottle (Or breastfeed). Burp, nappy check and put on floor to play. Now is awake time, no dummy use. At the first grumble, pick up and sooth and back down on floor to play. If another grumble - it's sleep time. If no grumble watch the clock for your awake time window (approx double last sleep time). Reoffer what's left in the bottle (Or top up breastfeed) and straight into bouncy chair.
Nap time:
Into bouncy chair. Bouncer at your feet, you on sofa with TV remote, phone and cuppa. Consistent tempo of bouncing with your foot, rhythmic and not too forceful. Keep on going. Reinsert dummy whenever needed and be complete relentlessness. Just keep going until asleep and do not stop or give up.
As eyes go, slow down bouncing. But stay there on sofa and watch baby. Because next important factor: resettle baby back to sleep as much as possible.
First sign baby is moving from deep to light sleep is face screwing up. Try to catch this - it's before waking properly, before any sound and before eyes open. At this point reinsert dummy and tap outside to encourage sucking reflex. Restart bouncing, gently at first.
It won't always work yo resettle bit sometimes it will. Always try. If not resetting then wake and go back to where you were before:
Wake - note time - feed - burp - floor time - watch for awake time window - top up feed - nap.... repeat, repeat, repeat all day long, every day.