Michael,
The Custom Filters are rather particular on syntax which is why many don't use them.
Try using the following for your Custom Filter to score email from the .download TLD:
.+\.download>$
Although .* would work in most cases there are unique cases where .+ would be more inclusive. The main part you were missing is the > at the end of the domain but before the $. We successfully use this along with many other newer TLDs.
Example 2 looks good, but when you are using Contains it is Case-Sensitive and Character-Sensitive. Therefore you may want to add all possible variations, one per line (i.e., Oprah, 0prah OPRAH, 0PRAH, oprah, et cetera).
The only other thing I can think of is make sure that whatever you put into the Header field, do *NOT* follow it with a trailing colon : as this is implied in that field and adding it to Subject: would result in looking for a field named Subject:: and never catching anything.