Note that many groups, and hikers, walk along the dirt road between Colpapampa and La Playa rather than the jungle trail on the other side of the river because it is easier and faster.
The advantage of hiking independently rather than with a group is that you don't need to decide such things in advance, you are completely flexible to change your route, your schedule and your night stops at any time. Also according to the weather.

Vedado or Habana Centro is first choice. Habana Vieja or Miramar is second choice. I stay in Jaimanitas/Playa Santa, because it is real Cuba with friendly Cubanos. Jaimanitas has Fusterlandia as a bonus and Santa Fe has the bonus of Marina Hemingway. I ride buses(huahuas) and take collectivos for CUP 1 peso or 50 CUP pesos, respectively.

People on Thorntree will say tourists are not allowed on Cuban buses. Cuban bus drivers will say "caca liquada/bullshit".

Is playa larga rocky? I see some pictures on google it is. They’re looking for that Varadero type of beach but without it being Varadero....

You do not need to book any excursions or tours prior to arriving. You can book them the day prior, from your lodging.

You also can book all your hotels, lodges via Bookingt.com or Expedia.com, or use AirBNB, VRBO, or a combo of all or some.

The caribe side these are great places-

Sarapiqui- The La Selva Biological Station Lodge in the park, if not, you can hike the trails with a guide from 8-12PM. If you stay in the park, you can access them 24/7. Outside the park, I like the Posada Christina Andreas, owner is top conservationist in country and host many worldwide study programs and scientist, researchers and birders.

Cahuita- The Alby Lodge

Tortuguero- I prefer the village, anywhere near the ocean for a nice breeze, Miss Miriam II is fine for me.

Cano Negro- Hotel de Campo, nice pool , cafe and great cabinas, with marina/boats and guides.

Pt Viejo- stay south of town and rent bicycles on this lazy afro caribe reggea vibe. Playa Cochles is a cool little village and surf scene, further down the coast a few KM is playa Chequita, and Punta Uva. AirBNB is best on this stretch south of PV IMO. Most the lodging is owned or managed by North Americans or Europeans and cater well to same...

Have Fun..

Haha! Classic! I took a taxi once from Havana to Playa del Este where I was staying. There was a huge hole in the floor and the fumes were intoxicating. Not in a good way lol! But I suppose that's normal for Cuba lol

Do you do business of any kind in Cuba to travel there so frequently or do u just love it like I do?

Go with a Yucatan trip or a Chiapas trip - I think too much to include both in 14 days. Stay in Cozumel once there instead of a day trip and back to Playa del C. Skip Holbox in favor of more time exploring smaller towns (maybe Izamal, Progresso, Sisal, the convent route, remote cenotes). Maybe stay in Tulum instead of returning to Playa del C. With airfare savings, consider renting a car more days - explore Sian Kaan, Coba.

There are frequent ADO buses from Playa del Carmen to Chetumal. Is your concern that the bus will be too slow (4h 40m en route)?

Playa del Carmen attracts a lot more tourists than Tulum; if Tulum operators have travel packages, then Playa del Carmen will have them too.

I would head for somewhere in the Azuero Peninsula which is about halfway between Panama (here we just say Panama when we are reffering to the city) and David. There are a few popular beach towns like Playa Venoa among others and some very traditional towns that would be great at Christmas like Los Santos and Chitre. There are also some very secluded beach towns if that is your thing. It is a little trek to get to from the interamericana but if you rent a car (even a bus is not too bad) it will be worth it. I would book way ahead of time because those town will be full of Panamanians on holiday. I hope you like fireworks...

My choice would be neither - there are several very attractive and relaxing places on the beach between the two - we have enjoyed both Koralia (several times) and Playa Roca.