Why would one not be straightforward about handling restaurant checks or bringing food to a gathering?

After I graduated from college, my parents said they wanted to cover restaurant meals when I visited because I had the expense and effort of airfare and a rental car. They sometimes did the "dropping hints" thing which makes my head explode -- luckily for all I raised the issue directly and it was never uncomfortable. My directness didn't always go well, and I wasn't always smart about it, but in this case it seemed to work out.

Same for bringing food or beverages to a gathering. If you want people to bring something, say so! Everyone is different. Personally, I find it annoying if people bring something that requires special handling, or doesn't go with the rest of the meal. I also don't want people barging around in my kitchen unless I invite them to do so. My mother was the same.

The issue of helping parents becomes more complicated with aging and illness, of course.