Hi all -
Really enjoy this forum, it has answered a lot of my questions. I have a question about the transition between vinyl siding and brick and if it should be caulked. I have a horizontal transition that was not caulked when I purchased the home. I wasn’t sure if this gap should be caulked or if caulking it would caused water trapment issues. Attached is a picture for reference. Any advice is appreciated!
No it doesn’t need to be caulked. If you must caulk it, leave weep holes for any moisture to escape.
The horizontal siding has been ripped down on the bottom course and they used a J-channel that acts as a gutter and directing all that water to what appears to be a window that is not caulked.
That should of been an under sill mldg. with a snap lock and flashing on top of the brick.
Proper examination of what is existing would indicate whether or not there was proper flashing behind the siding and if not, at least verify if there are weep holes in the brick and a WRB behind the siding and brick.
This detail area will leak like a sieve. 
That, and the top course of brick should have sloped away from the house to drain, IMO. 
Normally the brick should be caulked between the brick and siding to ensure no leakage will occur. Not really a requirement but just common sense.
Normally there is a 1" air space behind the brick veneer and the WRB. 
