Around 1 hour 40 minutes for these levels shown, I believe. Not knowing certain things can really prolong the attempts though. I figured out that by using the slow motion power (hold down L1) with Joe after throwing the boomerang (hold punch to charge, release) it does massive damage to regular enemies and bosses. Didnt test it on regular enemies but assume it works the same.
It seems punch and kick combos with slow motion do minimal damage to the boss, so I reccomend doing this method shown. Soon I think I will get a Zoom power that when combined with slow motion does massive damage to bosses but dont have it yet.
I reccomend purchasing alot of them for bosses. They cost 1500 for a 10 pack in the shop. If you waste them and then die on a boss stage, just reload your save to get them back. I was playing on emulation so I loaded the save state instantly from that save, if I lost a life. The price doesnt go up on the boomerang so you can keep purchasing them.
Deaths edited out as well as some aimless wandering with the puzzles.