I would think he'd want it resolved before then.

He's certainly not helping matters by asking that removal of the debt ceiling be included in it.

reuters.com - US congress has two days avert shutdown after trump rejects spending bill

is all that event planning performed by "essential" personnel?

They will be deemed essential by Trump. I know you try not to do this, but you've got to think like a narcissistic sociopath when dealing with Trump. The most selfish path is the most likely path. So the event planning will get done. Besides, isn't that mostly the Inaugural Committee, which is part of the campaign mechanism? Sure, security will fall under Secret Service purview, but much of the rest is the President-elect's job and not the job of the government as a whole.

then indirectly by closing a lot of things that guests and visitors would want to do while in DC.

What his invited guests do other than the inauguration itself is not important to Trump. And if some extra-important guest needs some special service, he'll just order that the requested service be opened. Someone important to Trump wants to visit the Smithsonian? He'll order a private tour. Paying for that is none of his concern. Those are underlings who are fungible and expendable.

Trump seems to want to go fast

He wants to go fast on his agenda. And his agenda consists of things for which he can claim credit or off of which he can personally profit. By creating chaos - by pushing for a government shutdown that is in place as he takes office - he can push the blame onto Biden and take credit for ending it. That just screams classic Trump. "Only I can fix it!"

If there are a sufficient number of adults in the halls of Congress to get the CR done by Saturday, it will get done. If not, I suspect we're looking at a shutdown until February.

--Peter