How to deal with a bossy elderly Chihuahua?

My Chihuahua is 14 years old; I have had him for about 7 months, adopted him from friends. He is cute as a button but of course he's a dog like any other and wants his way. He eats usually around 5 pm, and by 6 he starts insisting that I come into the bedroom with him. He wants to get on the bed, retire for the night and go to sleep after eating. He can't get on the bed himself because of his arthritic joints, He can no longer jump up or down. (I have not found a suitable ramp and am reluctant to shell out for one that may not solve the problem, because the issue is that he wants me to be with him, not just to get up on the bed himself.) So he starts whining and squealing -- he won't just lie down on his bed on the floor next to my desk (where he sleeps during the day as I work).

When i put him on my bed and try to go back into my office to work, he waits about 10 minutes and then starts making the funniest-sounding cries and squeals. He wants me to be there with him. If he had his way, I'd go to sleep at 6 pm! He can't hear well (selectively) and doesn't pay attention to spoken commands. (He will obey a gestural command at times, but he was never really taught anything--he won't come, sit, or stay.) I considered bringing my laptop into the bedroom to keep him company, but I really don't want to work in the bedroom. Should I just ignore him and endure his harassment until he gives up (he doesn't give up easily)? Or should I go with him and try to sneak out after he falls asleep? (Eventually he wakes up and realizes I'm gone and cries and cries.)

It seems as if the saying that you can't teach an old dog new tricks is true in this case.