My wife wanted a 5-flag holder so she got it.
EUREKA!!! The 5-flag version is now laying flat on the bed and printing without supports! Success!. Also featuring the universal wall mount.
UPDATE: 6-28-15, The 5 flag holder on thingiverse wasn't the correct version. Deleted the file that wouldn't lay flat with one that does.
PLA, 20% fill, a few manual supports, but shouldn't need supports now.
Fixed all problems with the 5-flag version, I printed a couple of them, no supports, and no problems. It looks a little questionable while printing, but in the end it meets the intended goals.