I've never heard of Lenco's "popping" out of gear. They have a one way clutch, and a high and low for each gear, that is what is shifted on each unit, compounding each ratio. The lever on the main unit id basically just forward and reverse and nuetral. Yes... it is possible to have 4 reverse ratios depending on how many levers are pulled in when the main box is in reverse.
Like what was said, when you let out of the gas at the top of a gear, the engine will go to an idle and "free wheel" where there is no engine braking. It is still in gear... I have two friends that race with Lenco's in 8 second cars, neither has ever had them pop out of gear. I think in high gear, it does have engine braking (not 100% sure...). Another guy has one that he drives on the street a fair amount, as well as races, running low 9 second passes.
You can upshift or downshift, with or without the clutch! One thing wierd is when the car is parked and engine off, and in any forward gear, it will roll forward if on a hill for example, to stop that you put it in reverse, and it won't roll forward (it can roll backward though!).
If I were you Jay, I would call Lenco and talk with them, get info from the horses mouth. Another option may be the "Jeffco" trans, which is very similar to the Lenco by design.
For the Liberty equalizer clutchless 5 speed, you do have to hold the shifter to keep it in gear in 1-4, in 5th gear it will stay in gear without holding the shifter... but if you let out fo the gas it will go to nuetral in any gear (I think even in 5th but not 100% sure...).
Clutch tune can be tricky, it would take some time the first time, then after broken in and a baseline set-up, wouldn't be too hard to adjust for race or street duty. I can adjust mine by myself in between rounds, maybe 6-8 minutes. Some guys run a stiff enough tune that you wouldn't need to adjust between street and drag, other combos may need a pretty good adjustment if on kill at the track.