Chugaev and Selenoxide Elimination giving different products

In class we are going over intramolecular elimination. In this question I will provide two similar reactants that provide a different mixture of products.


The chugaev elimination gives a 50/50 mixture of methylcyclohexene isomers while selenoxide elimination yields only one major product, but I do not understand why this is happening.


From what I can see, there is only one syn B-hydrogen available in both reactions. My professor went on to explain the significance of comparing the two reactions, saying that selenoxide elimination does not use heat while chugaev elimination does, causing a ring flip in one but not the other, which is understandable to me.


[![My analysis/work on the problem at hand](https://i.stack.imgur.com/3SWif.png)](https://i.stack.imgur.com/3SWif.png)


