The Late JD Hogg....season 3
Boss forecloses on the Duke farm after Rosco and Cletus make them late with the mortgage payment. Jesse accidently breaks the glass on the bank door so all 3 Duke men end up in jail. Right after that Doc Ronald Carney tells Boss he only has 2 weeks to live. Boss starts to worry that he might not make it to Heaven so he starts doing all kind of good deeds including letting the Dukes out and mailing off a bunch of charitable letters, documents and donations. Doc Carney finds out the person who is terminal is actually named Boggs from Hamiltonville and Boss is fine. Waylon says "That ain't gonna matter 'cause when Boss realizes what he's given away, that'll kill him". Carney can't get ahold of Boss so he keeps the charity drive going. In the meantime 2 bad guys steal the postal truck for the Social Security checks. The truck also has Boss's letters in it. When the Dukes tell Boss he's going to live at first he's happy but then sad. Bo and Luke catch the bad guys and Jesse was nice enough to tell Boss he'd still make mortgage payments anyways even though the mail went through anyways and he wouldn't have to since Boss was deeding the farm to him.
-- Flash dislike Boss so much that he even barks when he hears his voice on the CB
-- There are 3 episodes in a row that feature Boss, this one, Uncle Boss next and then Baa Baa White Sheep