Medical School/Pinnacle Dilemma

Jon and I are trying to decide what we should do. We got an offer that allowed us the choice to take a year off of school, which would mean that Jon could not only work for Pinnacle for another summer, but for the rest of the year in between as well. It's a great opportunity and we are not sure what would be best for us. We have made a list of pros and cons for both and have numbered them in order of importance.

Pros For Going to Medical School Now1. Jon would be a doctor faster.
2. We would have to move less and get to settle down.
3. Jon is already in 'school mode'.
4. Jon would be done selling.
5. It's a good time to buy a house.
6. We would be settled in before I got pregnant.
7. It is what we already had planned to do.

Cons for Going to Medical School Now1. We would unstable financially.
2. Our schedule would become busy more quickly.
3. It would be harder for me to find a job (in order to buy a house/condo).
4. We might not be in a position to buy a house/condo.
5. We might not get to go on our Italy trip.

Pros for Waiting a Year and Working for Pinnacle1. We would make more money and be financially stable.
2. Medical school has a rigorous schedule and it would be nice to have the extra time to prepare.
3. Jon would able to focus on school better because he wouldn't have to worry so much about money.
4. We would have a higher quality of life.
5. It would give me more time to find a job.
6. It would be great to have the extra 16 months to spend together.
7. It would be less stress to deal with right now.
8. We would get to go to Italy.

Cons for Waiting a Year and Working for Pinnacle1. Jon would have to sell for an entire year.
2. Jon might lose his Pinnacle fire, burn out, and have a hard time selling.
3. It would be longer until Jon is a Doctor.
4. Jon might not get the grant money that he would for this fall.
5. Jon might lose his medical school fire.
6. Jon might forget stuff he had already learned in school.
7. We would have to do more moving.
8. It would be longer until we would buy a house/condo.
9. We would have to move while I was pregnant.
10. We wouldn't know immediately where we would be moving.

We are still trying to decide what to do and we only have 1 more day to do it. So hopefully we can find an answer. Wish us luck! If you have any opinions we would be happy to hear them!