Hardie siding is brittle and difficult to cut so it fits neatly.

The design of the trim is good, but works poorly with Hardie lap siding. The trim installation is also really poorly done.

All the exposed edges should be eased (rounded a bit), and cuts should be clean and free of chipping.

Looks like a bit of hurried and sloppy installation, but if it's flashed properly, I doubt their will be any problems.

My concern is more with the sloppiness. Because it's at our entranceways it's pretty darn noticeable. How terrible does this look? And how can it be made to look decent?

Every trim and siding job is different of course and this is not a great one. But hardie is rough to work with. What should happen (IMO) is that trim should be put on after siding to cover the rough edges. But when it isn't, it shouldn't look like that. Siding can be replaced. They are like $10 a piece if I remember correctly. It is tricky to insert one in after the fact. I have cut out a small section and patched and caulked before.

When I get to my house I will take a pic of my trim around windows and doors for you

Cniss, looking at my job, I have to say your guys did a very sloppy job on the hardie. Here are 3 pictures from mine.

This first one is the side of my upstairs balcony door.