I play in many tournaments with multiple entries and often take the maximum allowed. I have done better in contests with all mandatory races as I make all of my selections prior to the first contest race and only make changes if I need to “stab” or if I am in the lead and can change to a horse I believe will win (regardless to the odds) to protect that lead. I have no problem with people taking multiple entries as it makes the prize pool larger. Does it give one an advantage? Yes and no. In a contest with all mandatory races a multiple entry player has a huge advantage if they hit a "cap" horse or one or two double digit horses on all/most of their tickets. In a contest with both mandatory and optional plays there is a definite advantage in the mandatory races and the player can choose two double digit horses in some of the optional races. In races with all optional races my thinking is the advantage is lessened as chaos can ensue as one decides what horses to put on what ticket. I witnessed the latter at the recent Horse Player World Series. I had one entry but a few of my friends had 2 or more entries and it got a little confusing at times. Only one person in the top 10 had more than one entry, James Benes. Here is a list of 16 people/families from the HPWS last weekend with more than 2 entries along with their highest finish. James Benes – 5 (10th), Robert Bertolucci – 5 (43rd), Craig Kaufman – 5 (191), Hinson Family – 5 (252), Dave Gutfreund – 4 (46th), Paul Shurman – 4 (102nd), Joe Corvi – 4 (103rd), Gwyn Houston – 3 (67th), Tom Blosser – 3 (216th), Scott Eyraud – 3 (292nd), Bonhoff Family – 4 (76th), Christopher Larmey – 3 (362), Steve Herres – 3 (270th), Dan Kaplan – 3 (183rd) Paul Caltagirone – 3 (321st), George Smith – 3 (491st) and Carm Adamino – 3 (572nd). Only 3 in this group received top 60 prize money: James Benes ($6,590), Dave Gutfreund ($988.50) and Robert Bertolucci ($988.50). James Benes also received $790.80 in daily prize money on day 2. I hope to qualify multiple times for 2012 as I would like to play 4 entries.
I don't play a ton of tournaments, so I'm no expert, but like you said - playing with multiple entries can mess with your head. It seems like every time I have tried multiple entries, I end up with a different 20-1 on each entry, and ultimately two mediocre entries.