sounds like we've had similar experiences. I put the Pi header on the wrong side of the PiDP-11 board: desoldering that was a nightmare - but I eventually succeeded, in no small measure thanks to Oscar's encouragement and a good number of suggestions from others in the PiDP11 group.
I've also recently completed my PiDP-8 without any significant issues - the only real problem was that a small bit of solder from one point fell into one of the holes for the header. But especially with all the experience of desoldering from the 11, fixing that was easy-peasy.
I was also a bit uncertain about the LED patterns resulting from the self-test - but several folk here were helpful in calming my nerves and assuring me that what I was seeing was correct, even though it didn't fully line up with what I was expecting from the "column" / "row" numbers in the test.
Momentary switches are all operated by temporarily depressing the lower part of the switch. So mount them such that you momentarily press on the bottom half of the switch to actuate a signal. People get this wrong regularly. The 6 momentary switches have their lower half sticking out to the front unless you depress them momentarily.
Once you get that clarified - I don't know if you plan to tape the switches to the board prior to soldering, as was suggested in one of the beige-o-vision videos for the 11 (IIRC)? I've used that trick several times - e.g., with the diodes and resistors - and it's (usually) quite helpful. (For some reason, several of the resistors supplied with the 8 did not want to bend very close to the body of the resistor itself, so that they would not always fully seat flush against the board. This was a bit frustrating, but not a problem in the long run.)
Taping sort-of works for the switches: but despite being very careful and everything looking as it should as I went along (I checked many, many times ...), I wasn't as satisfied with the outcome on my 8 as I had expected given the constant checks. Despite it all, an occasional switch is not sitting quite as perfectly flush on the board as I would like. It's certainly more than "good enough" - good enough that I don't feel compelled to go back and de/re-solder the minor offenders - but not quite as fully in line as I would like and think should be possible with still more care.
I'm ordering another when they're available - and hoping to try this approach to the switches instead.
Rather than placing all the switches in at once and then having a go at them as Oscar suggests (first just one pin at a time - excellent advice per se) - I'm wondering if it would work better to try, e.g., three of the far right and far left switches first. After making sure these are in good order, then work in in sets of 3-6 at a time. My thought is that the switches at both ends will provide something of a stabiliser when placing and soldering in the next set - and it will certainly be easier to make corrections along the way as needed rather than wait until the end, only to discover, as I did, that a few went slightly amiss.
I don't know if this sort of approach would work any better or appeal to you - but thought I'd suggest it. And maybe others have tried similar sorts of alternatives to good effect?
In any case - enjoy! Despite my perfectionist issues with an occasional switch - the overall results are more than satisfying aesthetically and certainly technically.