Tom's Goal, and his method

Actually it didn't look like he came up with any plan until the very end where he set up Bernie to shoot the Dane... he seemed to be making it up as he went.

1. We know Tom is not a killer or even violent - he gets pushed around and beaten by everybody and is shocked when he is told to kill Bernie and has trouble going through with it even though he knows Bernie deserves to die. He actually digs himself into a hole by not killing Bernie. When Verna tries to shoot him and is unable to do so, he asks her gently 'Not so easy, is it?' which indicates that he did consider killing Bernie but couldn't do it.

2. He didn't plan on any of this happening. He was forced to confess to Leo in order to convince him that Verna was using him.

3. We see him being outwitted again and again by the Dane who double checks on Bernie's corpse, tries to convince Casper to double-cross Tom, follows him to 'Drop' Johnson and uncovers Bernie's plot and is in the room when Tom tries to meet Caspar in private. Tom caught a lucky break in that Bernie killed Mink and put his body at Miller's Crossing and that the Dane was too caught up trying to kill him to talk sense into Caspar (here Tom had done his homework by putting the idea of betrayal into Caspar's head but it was a very close call.)

4. Tom had a plan for Caspar to be killed by Bernie but he didn't anticipate running into the Dane at Caspar's house. He got unlucky that the Dane intercepted him there but then got lucky that Caspar killed the Dane without listening to him fully.

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Yes, Tom cares about Leo and Verna despite his affected aloof demeanor. He is conflicted because he loves Verna and doesn't want to hurt Leo. Tom only reluctantly reveals his relationship with Verna in hopes that he will drop her and stop protecting Bernie which is causing friction with Caspar.

Once it backfires (sort of) he comes up with the idea to help Leo from the other side of the table. The Dane is Tom's equal when it comes to strategy and superior when it comes to might and killer instinct. Fortunately Tom is a keen student of people and he recognizes Caspar's weaknesses and how they can be used to manipulate him.

Despite curves from Bernie and The Dane Tom succeeds in saving those he loves even if it means he doesn't get the girl.

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Seems like Tom was loyal to Leo and wanted to save/protect him from Casper. Tom also knew that Bernie was a lying troublemaker and wanted him gone.

So far so good. Tom comes up with a very convoluted plan to accomplish all of this.
Why wouldn't Tom just kill Casper, Bernie, and the Dane? He had them alone many times, so getting to any of them was not a problem. He killed them later, so why not earlier?

I can see WHY Tom wanted things to end up like they did, but the goal could have been accomplished so much easier.

I don't think it's a situation of Tom having a convoluted plan so much as he has to keep adjusting his sails, figuring a new angle or way to manipulate his way out of the trouble he's in just to stay alive.

"I speak Spanish to God, French to women, English to men, and Japanese to my horse."

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They make a very clear point of showing Tom as someone who cannot just kill someone. It isn't until he was completely screwed over by Bernie at the end that he finds the gumption to do it.

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Tom wasn't an assassin. Killing was an absolute last resort. He was the advisor role to Leo and tried to avoid doing any killing himself. He had obvious conflicts with killing Bernie and thus the plot of the movie. He was fine with letting Caspar take care of Bernie to avoid and problems and keep the peace, but Leo couldn't see the light.

As other's said. It wasn't so much a plan as reaction to events...and a little luck.

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