I once read of 2 approaches to reasoning; the linear sequences (like a chain) and the web approach (simultaneously considering multiple inter-related variables). The former was associated with men's thinking and the latter women's stereotypically, though neither is exclusive to a gender.
-----I lean toward linear sequential thinking as I try to nail down each step. It's a bit reductionistic, but easier to articulate to myself and others.
Then there's the conceptual model of an onion with layers within layers for understanding a complex topic (such as Bible study). Like the linear thinking approach, it deals with factors roughly one at a time.
There's an old saying, 'Where you stand on an issue depends on where you sit.' Am I going on a solo dive trip, or taking my wife (and maybe mother-in-law) and our little girl? They don't dive, so an engaging topside is needful if they go (whereas I go to dive; the topside other than the live-aboard boat or resort isn't a big deal).
In other words, is it a dive trip (probably just me) or a 'dive trip disguised as a family vacation' (wife's phrasing)? Let's look at each. Note: I'm not taking care to list in sequential order.
A Solo Dive Trip Analysis.
1.)
It needs a compelling key feature. Has it got good, lush coral reef diving with pretty tropical fish (usually what I want) or does it have big animals (e.g.: large sharks, sea lions, etc...)? Bonaire is known for shore diving freedom, Little Cayman for reputedly the best diving in the Caribbean (but the outer atolls of Belize are comparable, and I hear Cayman Brac is really close plus some shore diving), North Carolina for sand tiger sharks and Jupiter for lemon sharks and goliath grouper, etc...
2.)
Total trip cost has to be affordable. Loved my Galapagos trip but will likely never make it back because that's a whole lot of money for one guy to go dive a week. All other things being equal, cheaper is a big draw.
3.)
A reputation for being the regional best. 'Best' may be functional (e.g.: ease of shore diving), not just lushness of the reef, but when a place has a reputation for being the 'best' in a region, that's a draw. Little Cayman in the Caribbean, Raja Ampat in the Coral Triangle, Lembeh Strait for muck diving, Bonaire for shore diving freedom...'brand' matters. Disclaimer: I've never been to Raja or Lembeh.
4.)
Travel time/hassles. Some Red Sea liveaboards are cheap, and at least awhile back airfare from the U.S. could be quite affordable. Why do U.S. divers keep heading to the Caribbean when many might say the Red Sea is better diving (at least if you do liveaboards)? Spending several hours on a plane, dealing with multiple connecting flights, that creates resistance to going. Some people find it hard to be away from work or family over a week.
5.)
Cultural ease vs. difficulty. Yes, foreign architecture can rock - love Curacao's Handelskade waterfront. Hawaiian luaus are famous. But places where English isn't near universal, 'squatty potties' and alternative approaches to butt wiping might be encountered if one gets away from touristy areas, very different cultural expectations (e.g.: degree to which you are expected to cover up), these things can be off-putting. Especially if the legal system has a reputation for being harsh with violations. Nice if the U.S. dollar is accepted everywhere. TLDR:
Exotic looking is a plus; actually being exotic not so much.
6.)
Ease of Diving. In researching Raja Ampat vs. Komodo, the latter had a draw because it's a household name and it'd be cool to see wild Komodo Dragons, plus our kid would remember daddy had been there. But neither is considered a beginner destination (I'm not a beginner), but have some drift diving but Komodo's has more intense drift diving (I ain't built for fighting current) and Komodo seems to be a bit more demanding...and Raja Ampat seen as that little bit better diving. So I'm planning a trip to Raja Ampat, not Komodo. The often deep diving of the Maldives doesn't sound appealing to me.
7.)
Solo Shore Diving. Bonaire. Curacao. CocoView Resort in Roatan. The option to gear up and go in at will is a powerful added draw. Resistance is solo diving is probably why I haven't done a dedicated Grand Cayman dive trip.
8.)
How Many Dives Can I Do? When I read about a less mainstream destination like Grand Turk (without a lot to do topside), St. Eustatius, Grenada, Puerto Rico, etc..., one of the key questions on my mind is how many dives can I do there? If I'm traveling alone and diving is the sole focus of the trip, 2 morning dives then laying in a hammock the rest of the day won't cut it.
Related topic:
big tanks are a big draw! 100-cf Tanks are nice, but tell me you've got 120-cf steel tanks! Aldora and Living Underwater of Cozumel are known for this.
9.)
Novelty. I like expanding my 'portfolio' of personal dive experiences. I've done 18 dives off Little Cayman via liveaboard, and only 2 Cayman Brac dives (both the
Keith Tibbetts wreck), so while CB has a rep. for the dives being a little deeper, even if I didn't plan any shore diving I might choose CB simply because I've done LC more and CB would be newer. Similarly, I have an ambition to someday dive the Bahamas...because I've never done that. Even though the Bahamas aren't considered on par with the Caymans for reef diving.
10.)
Safety. I'm mainly talking about risk for violent crime or a reputation for being 'seedy,' but malaria, tuberculosis, these things matter, too. It's reassuring if I can drink the tap water.
11.)
Ease of Planning. If you go to Rainbow Reef Dive Center's website, you can flexibly book your diving and a range of hotel stays. It's pretty intuitive. In Cozumel, you can stay at an A.I. resort, or book with Tres Pelicanos and have your stay at Casa Mexicana (or some other places) arranged and get good guidance on how to navigate getting through the airport, plus you'll be close to the dive shop and they'll get you to/from the marina in the morning. Liveaboards are often 'turn key' simple. One of my criticisms of Puerto Rico as a dive destination is based on my interpretation of trip reports that seem to lack these 'hit the easy button' options. Not everyone wants to independently research accommodation and diving. Be mindful if I've never been there, I don't know how many good restaurants are nearby and whether they're walking distance.
12.)
Air conditioning. If your location is tropical, this is non-negotiable.
13.)
Good Food Options. A liveaboard needs a rep. for good food because I can't go elsewhere. Land-based locations may if A.I. or it's impractical to eat elsewhere. I'm a glutton, not a gourmet, and budget is a concern. Mostly I don't want to be faced with uncooked fish, raw oysters, rare beef, unsafe or unappealing food, and I tend to avoid pork. Vegetarians/vegans seem common and food's even more an issue for some of them due to limited selection; some people avoid gluten.
Family Trips with some Diving.
Similar decision tree as above, so I'll focus on what's different.
1.) 2 Dives/day is okay, lest I get the dreaded stink-eye and 'I thought you were going to spend more time with us.'
2.) A topside resort with nice grounds and a kids' club is a real plus (e.g.: Sunscapes Resort Curacao). A hotel room is fine (e.g.: Hotel Caravalle in Christiansted, St. Croix) if nearby engaging activities and restaurants.
3.) A scenic topside environment with some 'road trip' options is a real plus. So the (non-alcoholic) beer drinking pigs and jeep tour in St. Croix, trips to Lion Country Safari, Jungle Island and Zoo Miami in Florida, public aquariums in North Carolina and such become important.
4.) Access to '1st world' level healthcare is more important traveling with a young child, or an advanced elder.
5.) Ease of transportation. We can deal with driving on the left side of the road, but how bad's traffic, how good (and wide) are the roads, does the system prey on tourists who have accidents, is it easy to find one's day, etc...?
Other People.
Not a thing with me, but people prone to sea sickness like short boat rides - the southern A.I. resorts in Cozumel, some Roatan dive boats, IIRC from reports Grand Turk, that's a thing.
Some people want to spear fish, and some don't want to see it.
Some people enjoy shark feeding/baiting dives, and some avoid them.
Some people enjoy drift diving but it frustrates some because they can't hold still awhile to compose macro shots, watch a single coral head for awhile, etc...