a friend purchased WinPilot, SeeYou, and
StrePla. He's become used to WinPilot, and has offered to GIVE me
StrePla. Can it be set up so "Even a Caveman" can use it?

Your friend may have inadvertently shortened your choice list, if he
kept the other 3 for himself.......

Simpler and easier do not exist, it's the nature of the software
richness and flexibility.

Ask the guys you fly with what they chose, they will be the ones to
help you in times of confusion.

If you already have desktop software for flight planning, get the
flight software which most easily shares the waypoints, terrain, etc.
set up on the desktop. And always spot check any transferred data for
accuracy. I learned that early with shareware solutions. In flight the
software products have equivalent functions, ease of use and their
data interface then become more important.

SeeYou Mobile lets you turn off any display feature which irritates
you, as do the others I'm sure. Keep in mind it has 2 map displays and
each is configured separately for whatever use you want to make of
that. Cruise with one map, thermal on the other.

Do you fly in various locations? Sharing the ship? Find the one that
lets you easily change sets of waypoints and airspace, terrain, etc.
The 'Profile' feature in SeeYou is quite good at managing named sets
of related files on the PDA and retaining personal display preferences
for multiple pilots.

Software locked to a hardware serial number is not as flexible in
'hardware failure recovery mode' as those which are not. A nit.

Keep ALL your data on SD or CF. And take a copy of that regularly.
Losing PDA power wipes memory, so have everything on external media.
Take regular PDA backups to both SD and desktop. I had an SD card
fail, it's ugly.

Keep your eyes out of the cockpit.