It is random. I suspect it involves all of these:
- wait til just before the draw closes, then bid on low entries items to increase your chance.
- participate actively, daily most likely to get the maximum bucks you can each week, that involves making new threads and then its a battle against the moderators for frivolous and duplicate threads.
- place more entries on items you really want. less on what nice-to-have, be disciplined.
I was sat on >5000 bucks and got below <4000 just by a few weeks of entering to the maximum and so had to curtail it back to not run out of bucks.
I have won total of twice, the odds are basically very low.