If you're actually writing software in assembly (as opposed to merely optimizing hot functions in an otherwise high-level codebase), in my experience MASM is the most pleasant tool for the job.

The most pleasant is the one you're most familiar with. I still use gas with at&t syntax.

MASM's niceties go far beyond just syntax, though

I last used MASM back in about 1989 (with MS C on OS/2 1.0). Do you have any hints on how it has changed since then? What is nice about it, and why does the debugger not match up to CodeView?