Current employment and housing on the island

Not sure what the elections have to do with your decision and I am not going to ask, but it is the same president for PR also and any decisions he makes likely will affect the island in similar manner. You are still in America.

Since you seem to be interested in answers from people currently in the island I will stay away from commenting further.
Give people a few days to see your post.

Riososo,

Working on Palo Alto I know what you mean about prices in the bay. We have our retirement house in PR and will be moving there soon.
As you may have read, jobs are very hard to find and without a good domain of the language it will be harder. As chefs you may be able to find opportunities in the metro area or even closer to Rincon where a lot of expat lives. I will suggest explore different parts of the island and see what fits for you. A year is a long time and it will give you time to aclimate and practice the language.
I can tell you, it beats the crazy traffic in the bay area and the fast live.

The economy is in a bad shape and finding a job is not going to be easy. Not being fluent in Spanish is going to make it even more difficult.

Then again since you guys can afford to live without income for quite some time it might be worth a try.
Renting a place to live is very affordable, especially if you look outside the metro area. Think out of the box and you might get lucky and be able to start a new life here on the island.
I ended up doing something completely different  and making 20 times less than I did in Europe but I love the place, been here 15 years and I'm not going anywhere..

We are always up for a good challenge! We plan to do just that. Check out the island and vibe to see if we want to live there. If so, then another trip and so on.

Sounds good! You'll find that most people are friendly and helpful. Getting to know them is a good plan-  the local watering hole and a couple of rounds of beer are a good start.  With a couple of drinks Spanish gets easier, too

If you rent a place in a rural area there's a good chance that the land lord will keep utilities in his name so you won't have to bother dealing with that but  instead either pay a fixed price or he will come every month with the latest water and "light" invoices and you pay him cash.

Since many locals are leaving the island there are plenty of places for rent (look for "se alquila" signs) and you will get a good rate.

Have you thought about opening up your own restaurant?

The private chef opportunity might work well for you if you focus on event catering. Because there are many expats moving their business to places like Palmas and Dorado, they often have people in for meetings and events....people must be fed. We have hired a chef to come in each day when we have board meetings and prepare all our  meals.... she brings all the food and we supply the kitchen and many of the supplies. Its a possible niche business but I will say, if you do this-be sure you clean up after yourself. It took us hours to clean up the mess from that last meal of churrasco! She won't be invited back because of that!

Thanks for the advice! Clean up is always mandatory! That is too bad, but always a good reminder.

I would consider that. I want to wait to get to the island and see what the culinary scene is like. I do not know all to much about it.

I've skimmed your first post. I'm retired with an at-home job and living in Tucson.  However, I do have PR and Bay experience, but both a very long time ago, and in the 60s, both PR and SF were livable, even nice. The breaking point for me will be not just killing Obamacare, but Medicare. If the Republicans kill either one, they will, in fact, be killing people at various stages of treatment. Imagine getting cancer treatment and then being cut off.  In the case of Medicare's demise (and possible SS cuts), I'm investigating Colombia, which has a good expat visa program and coverage under their universal system.  If Medicare is spared (I'd bet against it), a return to PR is possible and the tradeoff would be poor healthcare but cheaper COL (i.e., many houses and apartments vacated by those leaving the island, so it may be a buyer's market.

SS will not be cut; statistically, seniors are the strongest voting base... period. Obamacare may be enhanced & renamed, but it won't be fully repealed... the sky is NOT falling, and all will be okay, chicken little.