I love but also hate caulk, at some point I learned for reporting that ‘We recommend Caulking/Sealant anywhere two different building materials meet.’
Often when done, caulking is very ugly. I don’t think it necessary under eaves, overhangs etc…where there is practically zero chance of rain getting in. I think generally speaking caulking as stated is wise but for instance, where a stucco wall meets the vinyl j-channel at the eaves I don’t think that is a place to caulk, where vinyl siding transitions to a stone wall or brick area often if caulked it looks horrible and there hopefully is a moisture barrier back there but I know that is not always the case and we can’t confirm it, so ‘…we recommend caulk where they meet’. In new construction and old, hopefully there is a house wrap or drainage system etc… that allows moisture to drain if it enters in those areas. Some of these new homes I tour for fun I have seen the siding installed behind the window trim with no caulk, and it looks beautiful. To caulk it would most likely look horrible, but yes, water behind can be horrible too. I guess I am just looking for more input around this, and if anyone has a better standard entry you use in your reports. I see a lot of homes being built and being wrapped and know how important wrapping be done properly to help prevent moisture entry. I think we all agree that is the case and if wrapping is done properly why would we need caulking? I think many may just recommend it because we can’t confirm the house is wrapped properly, so caulking adds a layer of protection. At the same time, it just seems too easy to say ‘…We recommend Caulking/Sealant anywhere two different building materials meet.’ Please let me know your thoughts and have a great weekend!!
I have no idea who started this.
The cladding installation should follow specific industry guidelines or manufacturer installation instructions on how to treat transition areas for the applicable materials such as brick, stone veneer, vinyl etc.
For example, James Hardi siding specifically requires no caulk be applied at certain transition areas.
It’s one of those deals where a caulker doesn’t caulk like he should and the caulk use in places by the caulker is not always caulked right because the caulker did not read the caulking instructions and the caulker doesn’t know how to caulk to begin with so the caulking looks like caulk crap. 
That was a mouthful.
I have been removing the word “caulk” from my reports. That is telling someone how to do the repair which I try to avoid doing in writing. Instead, I say something like “Area should be sealed by a qualified contractor using appropriate methods.” During the walk around at the end I will sometimes tell the client to caulk a place here and there though.
Now that was one hell of a caulker. LOL
LMAO! Looks like a rental community I am familiar with!
When a home inspector recommends caulking all openings… homeowner caulks places like above a door drip cap and siding, where water needs to escape and not get trapped by caulk. Only specific voids should be caulked. In general, a properly built building envelope should rely on caulk as less as possible.