I think the dude is a great musician, beat maker, and producer. Like many of the best producers out there, he has a lot of soul, rhythm, experience, and a great ear. I suggest anyone who claims the FlyLo sound is easy to replicate should post an example of their best effort.

I don't think there is anything wrong with people trying to copy his sound, especially when they add their own flavour.
Anyway, here's my take on it.
For samples, he obviously uses a lot of soul/jazz vinyl, "ethnic" percussion, modular synth fx. Lots of compression, and sidechaining. Fairly standard hip-hop kicks, claps and tambourines instead of, or as well as snares. Not too many hats, but some ride cymbals for that laid back vibe.
There is usually some dusty noise in the background. Some people seem to be against using vinyl noise samples. I personally think a subtle vinyl noise sample can do wonders for a track. Stick an autofilter on it for that crispy burning vibe. He also uses subtle ambience in the background like tropical birds, tape hiss, flowing harps, chants, looped reverb tails, reversed melodic sounds, etc.
Some of his synths sound more like they're coming from a sampler rather than a traditional synth. Ableton Sampler is great for turning samples into freaky instruments.
For chops, the slice to midi function is great for creating a drum rack out of a vinyl loop. You can always repitch one of the sounds, then "copy to siblings". The same can be done to mess with velocity, spread, etc.
Even though a lot of his beats sound like they are simply played in without quantization, I doubt this is the case, especially if he's using a trigger finger, Ableton Lives midi recording is never really 100 timing accurate. Far from it. Still, you can use Live to add *some* quantize to your beats, basically tighten them up.
At the same time, the suggestion to jam out some beats and keep the best bits is an interesting one, but might work better in Live by recording and using the audio, rather than the midi. A lot of his tracks do sound like he is jamming and having fun, nothing is ever too stagnant or repetitive, even when he is apparently using loops on top.
He often seems to use simple percussion loops, but they sound lazy and come in and out of time. One nice way of getting this effect is to warp a percussion loop in Live, but make some of the hits a bit late (hold down shift and move the audio via the warp marker). For less predictability, loop the sample on 3 or 5 beats.
I think some of his drum/percussion parts are on a triplet grid, while others are on a standard grid.
Listen to "Fall In Love" (
http://www.youtube.com/watch?v=KwAa6I0dmA0)
That second kick, before the clap, is way late by most peoples standards. The kick itself is fairly compressed/limited, and there is a ton of "air" in the background. Throughout the track, that kick cuts right through the mix..