Help understanding discrepency between sys.dm_exec_cached_plans and dm_os_memory_clerks
FWIW - and I'm only posting this as a temporary answer because there's no way I could make this a digestible comment - I ran these queries and saw some discrepancies as well:

select cp.cacheobjtype, cp.objtype, 
  sum(cast(cp.size_in_bytes as DECIMAL(19,4)))/1024/1024 as sizeMB
from sys.dm_exec_cached_plans as cp
group by cp.cacheobjtype, cp.objtype
ORDER BY sizeMB DESC;

select mc.type, mc.pages_kb/1024 as pagesMB
from sys.dm_os_memory_clerks as mc
where mc.type LIKE N'CACHESTORE[_]%'
ORDER BY pagesMB DESC;


Most notably, the CACHESTORE_SQLCP total in the second query is less than the four Compiled Plan results in the first query, and there was substantial memory clerk usage under other cachestores as well. This is a lowly VM that doesn't have 300 GB of RAM but still demonstrates that these numbers do not always correlate and add up nicely.