Even though there are several HOFs on the site who have much more knowledge and experience about this game than me, but in an effort to answer the questions you asked, in my opinion, as I was taught (by the esteemed Amycox), the very first thing you have to accept is the fact that the 'names' of the players mean absolutely NOTHING!!!! It's their NUMBERS that count. More specifically, and generally speaking (with a few exceptions), a player's normalized numbers, in conjunction with their histories, will tell you a lot. Me, personally, even though I love offense, even at the expense of defense, I more often than not tend to play in offense-oriented parks, e.g., Hilltop, Fenway, Kauffman, etc., I'm a pitching guy who likes to build around top notch starting pitching because, for whatever it's worth, and of course I could be wrong, I just happen to believe that it's all about the pitching in the playoffs. However, in drafting your teams, you have to also be mindful of the fact that in order to MAKE the playoffs, you have to be able to score enough runs to win games. With this in mind, if you draft the right hitters whose strengths are conducive to potential success at the park you choose to play in, and if have good enough pitching, you should win your share of games. I'm not necessarily of the opinion that you fall into a "trap" when using low strikeout hitters in OLs against low strikeout deadball pitchers. But if you draft wisely and draft GOOD hitters for your park, with a few exceptions, I feel that it doesn't matter who the pitchers are that you're facing. The thing with low strikeout hitters going against low strikeout pitchers, simply means that more balls are put into play, therefore, in theory, resulting in more opportunity for your oppenent's defense to commit errors and minus plays and thus, allowing your team to advance runners. Again...I could be totally wrong. That's just the way I see it. But the bottom line is that you have to do what works for YOU and draft your teams in accordance with YOUR particular style of play and YOUR particular managerial mentality. Guys like Adam Dunn will strikeout a lot. Perhaps a little less in OL's than they did in real life due to the low strikeout pitchers, but they will, nonetheless, still strikeout a lot pursuant to their normalized strikeout ratio.