Extending the Sound of a Sample...

Any advice for a helping to a make a more natural transition when playing one shot sample chops?

you could experiment timestretching only the tail end of the chop.

For extending the sound of a sample and keep it still somewhat natural, you'll want something that can do cross-fade looping. I know that JJOS and Maschine can do this. Beatmaker 2 on iOS as well. I'm hoping we'll see this feature implemented in 1.9 but who knows, we could end up with a free expansion of booty clappin sounds instead.

Alternate loop could be an alternative. I find it very helpful in many cases.

Thank you for all your feedback so far...
How about Reverbs and Delays to achieve natural fading sound transitions?
I have been playing with these
Any hints/tips on these types of settings or specific Reverbs/Delays that you use to achieve desired effect?

Just use alternating loop for gapless playback (if you mean your hits are too short).

Thank you Fanu and Italian Beats. I'm going to try the "alternate loop" option when I get home from work tonight!