The best "retirement" situation I know of for former CO's is when the Branch farms them out to a (usually rural) Congregation that has built an apartment onto their KHall. The CO and COW get free rent and utilities. The Cong gets an elderly but well experienced and respected elder and his wife. Since they are over 65 yo they have free Government health insurance (USA Medicare) and if they had secular employment before going into the CO work, they receive Social Security (thought perhaps a minimal amount ie, $1000/mo). They are likely assured of a few cash gifts from any JW family that has the funds and some kind and generous brother in the cleaning biz might toss them a couple "easy" office cleaning gigs if they are physically able to do light cleaning.
They actually are probably a lot better off than the typical elderly JW couple that slaved away for the bOrg pioneering and living a meager existence waiting for The End(™) that never comes.