I thought I would post some information here from the Timeline I no longer really keep up with. It might come in handy.
1990 Trudy and Adrian get married apparently some time in the fall or late summer. In 'Mr. Monk Gets Drunk' Adrian goes back to the inn and vineyard where he and Trudy honeymooned for their anniversary. They are holding a wine tasting and making the red wine that was Trudy's favorite during this episode, and red grapes are harvested for wine making usually from the middle to the end of September. Considering that the grape stomping process takes longer than the machine process, they may have started making it earlier than the other red wines. It's possible that this episode took place anywhere from mid-September to early October, but I tend to think it was in late September. All of the other episodes for the first half of the fourth season appear to have taken place in the fall of 2005.
'90 is also the year that Dale loses his mother, goes to bed and balloons from 422 to 927 pounds over the next eleven years. 'Dale The Whale'
'92 Trudy was working at a paper, I think it was the San Francisco Times, from what I can see of the front page in 'Mr. And Mrs. Monk'. Adrian pointed out a desk and said it was hers for five years, and he pointed out a mark that he said he did, leaning over to kiss her and he spilled some coffee. He told Natalie he spilled something again seven years later, on Jan. 12, 1999 during an earthquake. '99 minus seven years means she worked there in '92, and she was killed in '97, so she could possibly have worked there till her death, but, In 'Billionaire Mugger', Adrian said she was a columnist for the Examiner.
'93 Trudy writes the article about Dale, he sues them even though he knew he couldn't win, and drew it out for a year so that they had to sell every thing they had, including their home, which he bought, I assume out of spite. I wonder why he didn't just buy the paper to keep his name out like Leland said he was known to do, it seemed he formed some odd fixation with Adrian and Trudy and seemed bent on destroying them. But he told Sharona that he sued them nine years before that episode took place, which seems to have been in spring of 2002. (On the 'Exclusive Content' section of Trudy's Case File, the exact publishing date for this story is given as Tuesday, March 9, 1993).
'95 was the last time Dale and Adrian had contact before 'Dale The Whale'- Dale asked him how
long it's been, and Adrian says it's been 7 years, but it isn't stated what this meeting was about. The lawsuit was presumably over the year before that.
'95 Trudy and Janice Ellinghouse wrote a story together on the dockworker's union that caused Jack Bollinger to become union president after he was their source and the former president (Ed Lemley) went to prison where he was still in Oct. 2005. Mr. and Mrs. Monk
As of June 21, 1997, Randy was still a sergeant working in Philadelphia PA, a few days after Darlene Coolidge married, then killed one of her husbands. Randy was the lead investigator in the case. The newspaper article that the captain brings from the photographer's business is dated June 21, 1997. More than once, references have been made to that event being six years prior to that, meaning Wedding happened probably after June of 2003. I think there is another error in here. Wedding first aired on August 19, 2005. Six years before, would have been 1999 when Randy would have been working in San Francisco. If Wedding was supposed to be taking place in 2003, then there is the problem of Natalie not coming to work for Adrian until 2005.
'97 November 11,* at 9AM Trudy is killed by the car bomb. (Billionaire Mugger, this date can be seen on a forensics report that Adrian is looking at). There are inconsistencies here- in 'The Candidate' one of the articles said Trudy was 35 when she died. In 'Dale The Whale', Adrian told Dr. Kroger that she only had 34 years, that Dale stole one of them. With her birth date being Oct 10, 1962, and her death being Nov. 11, 1997, she would have been 35 years old.


* In the episode 'Up All Night', a different date is given, December 14, 1997. Since they included the fragment of the date book with '530 Kelly Street' on it, as well as the list of items recovered from the scene that were only referenced in the police reports in the same episode where I saw this date, I am guessing that this date has been changed or will be irrelevant in the end.
1998 Captain Stottlemyer has to take Adrian's badge. In 'The Candidate', he said
'When I took you badge three years ago..." and a little while later, Sharona tells Miranda St. Clair that Trudy was murdered four years ago. I am guessing that he must have tried to work for the police department for a while after her murder but it became apparent that he wasn't well enough.
Also in 1998, Sharona started taking care of Adrian. In Asylum, which took place in August 2002, she told Oliver that she had been taking care of Adrian for four years, and Randy told Gail in Earthquake that he had known Sharona for about four years.
You can view the entire timeline
here, though I don't know if there is anything there that will be of use in this case.
Also, there is Teresa's
Remembering Trudy Page which I and a few other posters to this board contributed a good bit of information.