LAKE BUENA VISTA, Fla. -- The Cubs’ needs going into the Winter Meetings are pretty easy to document. Solutions to those needs are another matter.

Here’s a look at the biggest holes on the Cubs’ roster:

• Replacing Ted Lilly in the rotation: After the team traded Lilly to the Dodgers, a spot opened up for competition between Tom Gorzelanny, Casey Coleman and Jeff Samardzija for the fifth spot in the rotation. However, with the unknown status of Carlos Silva, who had a terrific first half of the 2010 season before heart issues and other injuries limited him in the second half, GM Jim Hendry must find innings eaters to pitch in the fourth and fifth rotation spots. Figuring that Ryan Dempster, Carlos Zambrano and Randy Wells are your top three pitchers, the Cubs must search for a diamond in the rough. They will scan former aces like Brandon Webb and Jeff Francis, both trying to revert to All-Star form after being sidelined with arm injuries. Webb, a former Cy Young winner, hasn’t pitched in the Major Leagues since Opening Day of the 2009 season. A shoulder problem has persisted until recently for Webb. The Cubs watched the former Diamondback throw in the Arizona Instructional League in early November. Webb, at his peak, was a sinkerball master, but now he has lost some of his velocity. Cubs scouts had him topping out at 86 miles per an hour when they saw him in Arizona. If the Cubs can’t find a functional veteran to plug in, the consensus is they’ll move relief pitcher Andrew Cashner into the rotation. The Cubs also feel that pitching prospects Jay Jackson, Chris Carpenter (not the Cardinals pitcher) and Chris Archer will be a part of the pitching staff some time in 2011.

• Replacing Derrek Lee at first base: In this category the Cubs hope to find a first baseman who drives in runs and bats left handed. Numerous free-agent candidates still exist in the market place. However, the Cubs missed out on Lance Berkman, who signed with the Cardinals on Saturday for $8 million. The Cubs also offered $8 million to Berkman, but one source said there were deferred payments in the Cubs’ offer. The Cubs really don’t have a first baseman of the future in their minor-league system, so signing a veteran to a short-term deal would be the prudent thing to do at this point. As these meetings open, the Cubs were looking at former Blue Jay Lyle Overbay and former Tampa Bay Ray Carlos Pena. Overbay is just a moderate threat left handed. In 2010, he hit 20 homers with 67 RBIs in 154 games. His .767 OPS is far short of what most teams look for from first base. Overbay’s 131 strikeouts are a concern as well. Pena is a terrific defensive first baseman -- though he came in under the Mendoza Line in 2010, hitting .196. That’s a pretty pathetic batting average. However, his power numbers were still good with 26 homers and 83 RBIs. Strikeouts are also a big concern with Pena, who whiffed 158 times last season. Pena is considered a top-flight clubhouse man as well. The other option the Cubs have examined the past couple weeks is a possible trade for Texas first baseman Chris Davis. Davis has big-time power, but also is prone to big strikeout totals. The Rangers are looking for a catcher in return for Davis.

• Replacing a setup man with a setup man: Cashner, a rookie, looked as though he had turned a corner in the setup role late last season. But, as previously stated, the Cubs may move Cashner out of the bullpen into a starting role. The Cubs are going to have to guess on left-hander John Grabow’s health and how effective he will be after returning from knee surgery. The team may need two middle-to-late inning relievers. The list of available, competent setup men is plentiful this offseason, but the salary base for middle relievers is another matter all together. With the signing of middle reliever, Joaquin Benoit by the Detroit Tigers, the price for an above-average middle reliever is around $5 million a year on the free agent market. Cubs icon Kerry Wood will be looked at as a possible addition. Wood will have to accept a setup role -- he was Cleveland’s closer for the better part of two seasons before getting traded to the Yankees in July. Wood and the Cubs would seem to be a good matchup. However, money constraints might hurt the team’s ability to bring back a reliever of Wood’s caliber.

Hendry will be active but somewhat limited during these meetings due to little payroll flexibility. A small trade or two might take place before the Cubs sign a free agent. Outfielder Kosuke Fukudome will be shopped extensively at these meetings. The Cubs are hoping that someone will take at least half of the $13.5 million Fukudome is owed in 2011. Team president Crane Kenny said on ESPN 1000’s “Talking Baseball” on Saturday that the team has ample cash and player resources for Hendry to add the components he needs for 2011. That type of bravado might be a bit of an overstatement, considering the Cubs already have close to 130 million committed to existing contracts and arbitration eligible players. Hendry might only have between $5-8 million to spend, after ownership cut payroll during their November budget meetings.