Temporary move for an almost 17 year old cat?

My cat Sassy will be 17 at the end of May but I'm in a bit of a pickle deciding what to do. I attend a school in St. Louis and my parents live four and a half hours away in Chicago. I've had my cat Sassy ever since I was three and he has always been known as my cat. My parents are great caretakers and love him very much, but I decided not to bring him with me to St. Louis when I moved into my own condo. About five months ago I adopted a year and a half year old cat named Lucy and both Sassy and Lucy became fast friends. In the beginning of February my parents are going on a two week vacation to Hawaii and we were trying to decide what to do with Sassy. I had a friend offer to come over and take care of him, but my parents and I have concerns about whether or not she would be able to come over as often as we hoped. He has never moved and been in the same house all of his life. He is a very active, healthy cat and it is always hard to believe he is so old! He is only on a few medications for behavior problems (he tears out his hair, a problem he's had for many years now ) and his hyperthyroid (he has had this problem for four years). My parents and I are trying to decide if they should bring him down to St. Louis to live with me and my other cat Lucy for a month or so while they are on vacation or if we should just hope for the best with my friend for the time that they are gone. Any help would be greatly appreciated! 

Normally, I would say this depends on the temperament of the cat, but two weeks is a LONG time to be left alone. I think if your friend can't go over to your parents' house at least once a day to provide fresh food and water and spend some time playing and interacting with him, then you should consider bringing Sassy to your place IF you don't think the transportation and change in environment would stress him out too much. It's a tough call.

ETA - oh, and your friend would have to be comfortable giving Sassy medications.

17 is old to be moving 'temporarily' I know he would be MUCH happier if he could stay at home. I would talk with the friend and explain that he is old and used to a routine and if she has ANY problem with thinking she can't make it at times now is the time to tell you.Maybe you could line up someone else to check up on him and her too. Bringing him to your place could work as a last resort, but I know it would be hard on him. Good luck and God bless.