It surprises me that you have read Silmarillion more times than any of his other books. This is the one which (imho) is the most difficult and least interesting of his books/ Perhaps that is because , after reading The Hobbit and LOTR, I came to it last and - expecting another interesting story - ended up with a different type of book altogether.
I agree that most of hearken back to the 'good old days' (even if they weren't always that good!) and The Shire epitomises those carefree days of Summer in the countryside.
Ive read the Silmarillion and true, parts of it were not an easy to read but overall , it has majesty and power all its own . As ive said before, I wish J R R Tolkien has made this into a saga such as LOTR . With the amount of material here , he would gotten 3 books. I think that in that form, it would it would been the equal of LOTR.