WELCOME!
289 engines had two different bellhousing bolt patterns ( 5 bolt or 6 bolt ) if you have a 6 bolt, things are going to be much easier.
6 bolt transmissions are very pletiful, as the same bolt pattern was used on small blocks from (IIRC) 1966 thru the end of the 302/5.0L run in 1997. So you can bolt up an AOD (need a spec flexplate and a LOKAR cable kit for the THROTTLE VALVE CONTROL [looks like a kickdown cable])
if you wanted to go with a 5speed manual trans, you can use a T-5 out of a 5.0L foxbody Mustang (1985-2003)
5 bolt blocks become a near impossibility for an automatic OD. but you can get adapter plates to mate a T-5 to a 3/4speed bellhousing for a 5 bolt block.
ALSO>>> did anyone else mention that we (ALL OF US) love to see pictures of the trucks, NO MATTER WHAT state of disassembly/disrepair they may be in?