Should I just put some clear caulk over it to prevent water intrusion or could this be a sign of a more serious issue?

There were, however, a number of large items, including leaking plumbing, a rotted second floor deck, and water intrusion from the deck into a bedroom.We decided to hold off on the appraisal until we could get some estimates on the work to see the extent of the work required and the cost.  

The job is replacing a 6 ft. high retaining wall behind a house that has deteriorated over the years and is leaning pretty badly, and has caused water intrusion in the basement.  

On an unrelated note, quarterly inspections seems overly intrusive to me.

Open cracks plus a humid climate that gets heavy bouts of rain creates all kinds of problems from moisture intrusion.

On the flip side there will also be a group that won't, not because they don't want to donate or contribute but because they may feel like it is intrusive on their lives.

I think it's too intrusive for the first line or two.

If I’m not being intrusive that is!

Some DIY things you can do are to check for water intrusion.  

You can check them out on Amazon.If you are looking for a less intrusive method try a Thermo Fogger.