This question brings up an obvious point some people forget at times -- nothing is done in a vacuum. Sometimes trading "better" players to get "inferior" ones might be more beneficial to your spot in the standings. Remember, it doesn't matter if you win the homer category by three or 33, you still get the same amount of points in a rotisserie league. Dealing from an overwhelming strength to shore up a weakness often makes a lot of sense.
Straight up I'd prefer Holliday over Upton -- by a lot.
Straight up I'd prefer Kinsler over Phillips -- but it's pretty darn close.
In this scenario however...
Last year Phillips (16) and Holliday (nine) had 25 steals.
Last year Kinsler (15) and Upton (42) had 57 steals.
Per 162 games in their careers ...
Phillips (23) and Holliday (14) average 37 steals.
Kinsler (28) and Upton (40) average 68 steals.
Clearly, if the goal is to improve your steals total, this is a move you have to make.
There is obvious risk however. Holliday will hit .300 with 30 homers and 100 RBI while Upton could hit .230-15-60. I personally think Upton has a legit shot to be a dominating force this season, he's a 20/40 threat in my mind, but their reliability grades couldn't be more different. I'd also make the argument that the upside with Kinsler is immense, we saw what he could do in 2009 when he went 30/30, but he's also played more than 130 games just once in five seasons. As for Phillips the ceiling may not be as high as it is with Kinsler, but he has averaged a mighty impressive 21 homers and 24 steals the past five seasons.
Given your situation, and your stated need for speed, I can support this deal as long as you have enough batting average strength to take on the potential downside that Kinsler and Upton could bring.
Volquez was a star in '08 with a 17-6 record, a 3.21 ERA and a mouth watering 206 Ks in 196 innings. He struggled in '09 before being shut down due to an elbow issue that led to Tommy John surgery, and last season he wasn't much better in his return to the bigs. In fact, over his last 21 starts the only thing that stands out is his still impressive K-rate: 8-5, 4.33 ERA, 1.42 WHIP, 9.13 K/9. He's also really struggled to throw strikes with a walk rate of 5.37 per nine the past two years. No matter how dominating your stuff is you simply cannot succeed long term when you issue that many free passes. Some of that lack of control can be blamed on the injury and working his way back into shape, but even when Volquez dominated in '08 he still had a BB/9 rate of 4.27, a full batter above the big league average.
Hamels, for some reason, gets about as much love as Paris Hilton at the Academy Awards. Last year Hamels was 12th in the NL in ERA (3.06), had the same WHIP (1.18) as Clayton Kershaw, Johan Santana and Chris Carpenter, and had a career best 211 Ks, sixth in the league. Flat out, this guy is an ace, even if he doesn't always get the love that he should in fantasy leagues. He is a safer and vastly superior option when compared to the Reds' Volquez.
But what of the cost? Converting the dollars to the standard $260 scale, Volquez would be $8 and Hamels $23. Obviously, Volquez is a tempting hold given that his cost is 1/3 of Hamels. Would I pay $23 for Hamels in a keeper league? I would. Would I pay $8 for Volquez in a keeper league? I actually answered yes before I finished typing the previous sentence. Without knowing how long players can be kept, if there are any salary increases in successive years, how much money you have invested in your other players, and without knowing who else is on your staff, I'd keep Hamels. If everything breaks right for Volquez we've seen that he can be an elite level producer, but Hamels is already there. I know the cost is significant, but in this case I'd go with the higher priced ace from the Phillies and sleep more comfortably at night.
I get a version of this question every once in a while, and I'm afraid my answer always disappoints -- there is no single way to do a baseball draft. There are general rules, and I'll get to them in a second, but there is nothing like there is in football, where you can basically say go running back and wide receiver in the first two rounds and defense and kicker in the last two.
There are many reasons for this. (1) There are more positions to fill in fantasy baseball. There are six main starting positions in football (QB, RB, WR, TE, DEF and K) while there are eight in baseball (C, 1B, 2B, 3B, SS, OF, SP and RP). (2) There are more players drafted in fantasy baseball -- sometimes as many as 10-14 more. (3) There is less certainty in some respects. In football when a RB goes down you know who the team will turn to for 20 touches the next week. In baseball, when a starter goes down, there is often a mix and match scenario that takes place, in addition to there being nothing akin to the replacement player being given a ton of touches and work at the goal lline. Simply put -- the situation is more variable in baseball.
As for some general rules, here is what I would suggest:
(1) Never draft a closer in the first couple of rounds. Don't wait until the last round like you would with a kicker, but there is no reason to jump into the closer mix until the middle rounds of a draft.
(2) I would not take a starting pitcher in the first round. Moreover, in most scenarios, I wouldn't take a starting pitcher in the first five rounds of a draft. This is not a hard and fast rule of course, but I rarely deviate from this plan unless I'm in a scoring setup which favors pitchers. In a standard 5x5 setup, there will be plenty of pitching available in the middle rounds.
(3) I would never take a catcher in the first round. I probably wouldn't take one in the first couple of rounds actually. Catchers are so susceptible to injury, especially foul tips to their hands or issues with their knees, that consistency from them is elusive. It's also not at all rare for a starting catcher to play 75 to 80 percent of their teams games, and that dampens the ability for them to post strong counting totals (especially in the RBI and runs scored columns).
(4) While paying attention to position scarcity early on, at least in the first couple of rounds I'm still targeting the best players with my first few selections. As an example, I'm not going to draft Jose Reyes in the second round if players like Matt Kemp, Justin Upton or Andrew McCutchen are still there. Reyes might play shortstop, a position that is in arguably thinner than the outfield, but if I have Kemp, Upton and McCutchen ranked ahead of Reyes on my draft board, I'm still going to go with the outfielders.
Have fun with it -- and welcome to the world of fantasy baseball.