As for the tranny popping out of 5th....well...if it was my car i would fix it. You need to fix it because IF 5th is stripped out...than the shards of metal will kill the rest of your gears. However the big question here is...is the car worth that much to you with the SR-5 in it....
The transmission is mostlikly leaking fluid at the seal between the tansmission and the drive shaft...or at the seal between the input shaft and the rest of the tranny....anyways...dropping a transmission down from a car is nothing to do.....and those seals are nothing to replace so i would say...look at the seal between the drive shaft and the rest of the tranny first...and if it isn't leaking...then you should drop the transmission down and replace both seals....and while you have it down....go ahead and open it up to look at the gears....BUT...if you open up the tranny you have to replace all the gaskets...so you need to have those on hand....
i know on a 4A-C it is difficult to take the oil pan down because of the transmission mounts that attach to the bottem of the engine...but all you have to do is look under the car...and if anything is blocking the oil pan to come down...it may be fairly difficult....or not soooo if the oil pan looks like it will come down with no problem..then it mostlikly will come down with no problem...
sorry about all your car trouble

...but MAYBE magic fairies will come down....and give you a brand spanking new car..haha