Your son's age 14, which a little quick Googling indicates some might set a depth limit of 60 feet for. From
ScubaDiverLife.com's article:
"However, once certified, the rules of diving are different depending on the student’s age. Until age 15, all divers are referred to as “junior,” no matter how many certifications or dives they achieve prior to their 15th birthday. Junior Open Water divers age 10-11 can only dive with a parent, guardian, or PADI professional and to a maximum depth of 40 feet (12 m). Junior Open Water Divers age 12-14 years old can dive with a certified adult other than a parent, guardian, or PADI professional, and they may dive to 60 feet (18 m)."
I'm not weighing in on whether you 'should' obey that recommendation/guideline or not. I'm saying before booking dives with a dive op., ask and see whether it's going to be an issue.
The Florida Keys have good diving that's fairly shallow and could work well for you. Keeping in that depth range wouldn't be a problem shore diving in Bonaire, either.
It should be a moot point soon - from a PADI article
Scuba Diving Lessons For Kids: "
Junior Diver Certification “Upgrades”
After the age of 15, depth and buddy restrictions default to those of a regular PADI Open Water Diver. Divers who were initially certified as a junior diver and wish to receive a new card that simply says “Open Water Diver” can order a replacement from their PADI Dive Center or
PADI’s website. The new card will automatically be printed without the word “Junior” based on the diver’s age when the card is ordered. There is no special action that needs to be taken during the order process to receive a card to get a card without the word
Junior on it."
On another page, they note the Junior AOW depth limit
for the deep dive: "Advanced Open Water Depth The Advanced Open Water Diver course includes one deep dive. How deep? The answer depends on your age, local regulations and dive site depths.
- The maximum depth for divers 15 or older is 30 metres/100 feet
- For divers 12-15 years old, the maximum depth is 21 metres/70 feet
"
In fact, to make sure you 'qualify' for (i.e.: are allowed to go on) deeper dives at some operators, you'll probably want the whole family AOW certified at some point.
What gear helps to get diving vs renting?
Dive computers, so you're familiar with the interface - I think you said you've already got those. Masks, because everyone's face is unique, and a leaky mask is aggravation. Boots and fins, especially if you have atypical size feet (I wear a size 15 and use Deep6 Eddy 2XL fins). Anyone who needs a wetsuit may like having their own that fits (plus, no matter how well they're cleaned, be mindful that peeing in wet suits is a fact of life - you may not care but your wife might). The buoyant effect of water (and I would imagine horizontal trim) moves more blood into your torso and chest, triggering a diuretic effect (i.e.: makes you pee). You don't need a weight belt if you rely on a weight-integrated BCD.
Don't buy tanks till you know how much local diving you will do, whether you need a larger capacity tank, etc...
Before you buy BCDs for everyone, do some reading on back plate/wing setups. I'm not saying they're better and you should get one, just that I'd like you to know about the option. Lots of people like the common jacket BCDs.
Oh, get everyone an SMB and a finger spool to tie it to. For ocean diving, it's a good habit to always have an inflatable marker on you. Little diver heads poking out of the water are hard to see.