Does caulk get too old to use?

[Murrmurr]

If it's rotting, you can't tell it.

Sounds like it's shrinking, though. Wood will do that over time, due to exposure.

Gary O' has a good idea. Paint or sealant, both will protect the wood. There's no rush on that, though. Go ahead and apply the caulk now, but at some point you should apply something to protect the wood from the sun, wood-worm and other bugs, rot, and moisture.

 

[Gary O']

If it's rotting, you can't tell it.

Just poke at it with something pointy

I usually run a two inch screw halfway into the wood
Then pull on it
If you can't pull it out by hand, you've got something to work with

Back the screw out and fill the hole with a bead of caulking or spackle

I've restored quite a few old pillars

 

[AprilSun]

Since I've had time to think about it more, I have decided I will get someone to come in and do what's needed. This way, I will feel better about it. Thanks everyone for your time and help. At least I know the caulking is still good!