Compression check can't hurt and it will tell you more of the truth, however, there are some things you can know just by starting the engine.
If it starts on its own, it has good compression in at least one cylinder. If it runs rough but smooths out in a minute or two, it likely has poor compression in one or two of the other cylinders. That means the engine is marginal and on it's last legs, needing a rebuild soon unless you are willing to start using start boosters, which is what I have to do to get my D-17 started. It cannot start on its own even hot.
Now, if it's running smooth and working but you suspect it might be getting a little long in the tooth, start saving your money now for a rebuild or a rebuilt engine and try to find someone that might help you do an engine swap on it.
I know this is probably not what you want to hear, but it's really up to your intuition as to when it will need a new motor. You can always get a case of frosty adult beverage for a buddy that knows what they are doing and have them check it out for you if you are unsure.