You can look for two basic issues when inspecting your mounts:
1) Unusual damage: rubber deteriorated, broken, detached, etc.
2) Normal wear and compression: Depending on you motor and and you mounts, you can measure that remaining space/gap between the top and bottom part of the mount (a diagram would help, but I don't have one!). I "think" that is must be >= 3/16" (for my 75 & 100 mounts for my 3GM30F).
Assuming no outright damage, check the remaining space under each mount. On my 1987 Legend 35, I assume the mounts are original, some of the mounts are at the very end of their lifespan. The rubber has compressed over the years, until 2 of my mount are at the limit. When I bought the boat, I have a feeling that it had not been aligned for years (ever?). I was totally unable to align the shaft because I had raised my mount to their limit on the front two mounts, and the shaft was still not aligned. I had to build shims to place under my front mounts to allow me enough adjustment range to get the shaft properly aligned. Even still, my engine was near the top of the mount bolts (which is undesirable).
I expect that I will replace the mount in the next few years.
Chris