There is no short answer....there is only a dissertation.
There is no better way to improve yourself as a handicapper than to learn to watch races well. The only way to do this is to watch races endlessly. The first thing you should do to teach yourself is watch as many races as possible, from both the pan and head-on angles, and take notes on EVERY horse in the race. Mark down what paths they are on while going around a turn ( each turn in some cases ) and also note any obvious trouble they have ( gate trouble and intrarace trouble ). A great deal of this is " make work " but over a period of time it will teach you how to watch a race.
Obvious trouble is one of the trickiest and most misunderstood occurances in racing. People tend to greatly overvalue it, especially when it happens to a horse they bet on, and invariably cost themselves money by adamantly betting such a horse back in the future. It is very important to accurately understand just how much specific trouble cost a certain horse. On this level I will give two recent examples ( and obvious ones ). Sweetnorthernsaint was bumped around at the start in the Kentucky Derby and lost not just a couple lengths with the trouble, but significantly more lengths in positioning in the race. He was six or more lengths out of position early and spent the next six furlongs working himself to a contending position. Not surprisingly he was empty late in the race. Oonagh MacCool had a similar bad start in a six horse stake at Gulfstream late in their meet, but recovered very quickly, and lost no significant position due to her start. Not surprisingly, she was still able to run her race. So, what I am trying to say, is that you cannot judge even similar trouble equally, but must analyze in every specific instance how that trouble affected a horse.
Another thing to think about is the trouble in association with a horse's overall trip. Suppose you bet a horse that saves ground behind a contentious pace in a turf race, only to be blocked when entering the stretch and forced to steady angling out. Yes, the steady may cost him ( or her ) a length or so, but think of all that was gained by the rest of that horse's trip, and all in all the horse probably got a very good trip. Many people will only point at the trouble and not understand that in the total concept things went better than average for that given horse.
" Wides " are another eternal argument. Many horses are intimidated by running inside, so while at a cursory glance you might tend to upgrade a horse that moved three wide, while downgrading a horse that stuck to the rail, the wider horse may well have had a free and unencumbered trip with the inside horse getting a trip that prevented it from running its best race. These situations can also be surface and/or very much particular horse specific. It is up to you to teach yourself to understand which situation came into play in a given race.
None of this stuff is easy, and it can be very interpretive, and you will not always make the right determination, but the more races you watch carefully the closer you will get to a desired level of understanding.
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