I think the described runtime errors occur because no proper "reweaving" could taken place on startup.
The logs (catalina.out) warn about this:
This error makes sense. Since the aop.xml from the SpringFramework spring-aspects.jar does not include AnnotationDrivenStaticEntityMockingControl in its Aspect list. Also its been applied through our static weaving (CTW) at compile time. However this should not resolve the final woven type in such a state that's its causing such weird runtime errors..
[TomcatWeavingInsightClassLoader@11a921b1] error aspect 'org.springframework.mock.staticmock.AnnotationDrivenStaticEntityMockingControl' woven into 'com.company.business.domain.offer.offer.OfferStatus' must be defined to the weaver (placed on the aspectpath, or defined in an aop.xml file if using LTW).