1.) Betting underdogs has obviously been a profitable experience for you. What are the major factors you consider when finding value in an underdog?
There are numerous factors when looking at a baseball matchup but I tend to find the best value on the "ugly dogs". I have won numerous times this season on teams like Houston and Miami, these are teams that no one likes to touch based on the fact they are simply not very good. Because of that, we get a lot of value based on the favorite being extremely overpriced. Linesmakers need to make these big adjustments because the public is typically all over these heavy favorites that are classified as the "sure thing". There is no such thing though as even the worst teams in baseball win 60 games per season so we need to find those spots and exploit them. I am +$13,009 on the season solely betting underdogs and this strategy is explained in much more detail HERE. (link to https://experts.covers.com/Articles/ada27cc470334e8cbfc5b8114aba3aed)
2.) Are MLB totals more profitable than sides? I have bet a lot this season on unders and have won most of them. For me the sides feel like a lottery, because it is not easy to score runs in MLB.
This is a very interesting debate as some people stick to just one or the other while others will mix in both sides and totals. For me, I am just a side play bettor in baseball and there are reasons for that. If I were to play totals, I would go your route and play mostly unders because that is the contrarian style and that is what I am about. There are two reasons I don't though. You mention scoring runs is hard in baseball and that may be the case in some instances but all it can take is one walk or one error to get an extra baserunner or two and that can lead to a big inning. Baseball is a game of inches and while that can affect the sides, I feel it affects totals much more because they are such low numbers. Second, there is no clock in baseball. Betting unders in other sports is a superior scenario as a low scoring game is harder to push over when time is getting short. In baseball, there is no time therefore an over bet is never done going into the ninth inning, or the final 11 percent of a game where in most other sports, those bets can sometimes already be dead.
3.) Why do both “experts” and amateurs continue to believe that the correct way to bet baseball money lines is to add the juice to favorites and play a flat amount on underdogs?
Adding the juice to favorites can be suicide in my opinion. Over the course of many seasons, favorites win 57 percent of the time so the breakeven point is about -132. Laying -132 to win $100 may seem like easy money but there are some who do not want to risk that amount of juice. By flat playing it, the profit would have been less, right around $76, but if the game loses, there is just the $100 at risk. Both situations would bring in an ROI of 76% if it wins but by flat playing it, while missing out on 24 fewer dollars of profit, we are avoiding 32 percent more risk. It can work the same for underdogs. These plays do not win at much as underdogs win on average about 43 percent of the time. Cutting down on the unit size will cut down on the risk with a loss but it will not cut that much out on a profit when it wins.
4.) In baseball which starting pitcher statistic should I be paying more attention? and in general what's the more important thing I have to check in a game to make a better prediction/bet?
Most bettors will look at a starting pitchers ERA and think that is the main stat to look at. My feeling is that a starting pitchers WHIP is more important. The ratio takes walks and hits into account so fewer baserunners means fewer chances of runs being scored. There are pitchers that get hurt by home runs which will obviously impact both ERA and WHIP but a pitcher with a low WHIP will have a lower ERA in the long run based on the fact fewer baserunners are involved. As for the second part of the question, there is never just one important thing to look at as there are numerous factors that need to be looked at. This includes bullpen performances, past history against teams and/or pitchers and lefty/righty splits just to name a few.