Alternately, I've experienced weirdness with Wing Commander I in 0.73 and 0.74 in Windows 7. I escorted a Drayman transport to it's jump point, it made the jump successfully (I waited till it did), upon my return to Tiger's Claw during debriefing I was told it was lost. This happened on another mission where I had to escort a transport back to the claw. I made it back, transport is beside me right before I land and in debriefing I get chewed out for losing the transport!
On one occasion after finishing a mission I went into the bar and there were 2 Lt. Tanakas at the table, then the game crashed.

I tried running it outside of DOSBOX on the oldest rig I have, a Pentium II 400 MHz with Win98 but the game runs ridiculously fast. It ran fine on the 486 I played it on originally and other games I have from that era (Commander Keen, Wacky Wheels, Raptor call of the shadows) run fine on the PII and DOSBOX.

Sloppy programming on WC and I suspect WC2 game.

i've had the WC2 speechpack freeze me on a real DOS machine too back in the day.

You can tell loadfix how much memory to consume, try something like loadfix -20 or -32 or -16 etc.

Well I was about to point out that I've tried loadfix with various parameters and each trial takes a long time, but I tried loadfix -20 for kicks, and I got by the hump that time. Thanks.
Incidentally, what happened next was a cut scene, so it could be that this is the sort of thing that causes freezes and such sometimes.