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From your starting location and not spending a large amount of your budget on flying nor a high cost on vacationing and still have high standards of amenities, Panama would be a good fit.
Any place you're thinking about, it would be good to try it out first, perhaps for a few weeks. We're going to Thailand, Cambodia and Laos in about 6 weeks--I'd never want to spend 4 month anywhere that I haven't already visited, especially somewhere like that.
I'd add Belize to the mix for Central America. And perhaps Uruguay in South America (haven't been there, but friends have.)
Warm and relaxing...well that doesn't really narrow it down much, lol. One I can rule out, though, is New Zealand. I've been and it's a beautiful country, but for a 'beach vacation' not what I would choose, if you want warm waters or warm weather. On the coast, it's often breezy and chilly, with highs typically in the low 70s, and often in the 60s. Waters even off the North Island will be chilly by tropical standards (or even what you're used too off the east coast in August), but it's great for other water-sports. NZ is more a place to see nature, explore, be active, not the place to lounge on the beach, eat cheap food, drinks, a lot of culture.etc (it's also as expensive as Australia being first world). For that you're better off going to South-East Asia.
Australia would be more up your alley: avoid northern Australia, including Queensland, as this is the wet season...plus in the northern beaches you can't swim because of stingers. It's expensive compared to Asia, but we have many backpackers and holiday homes people rent out, as well as reasonable long-term apartment rates. Anywhere south of Mackay would be preferable this time of the year.
Since you've been to the Caribbean, perhaps you might want to try out South-East Asia. Thailand, Malaysia, Philippines, Indonesia. Internet won't be a problem, most resort areas have good internet connections. You have the culture, and great food, especially Malaysia and Thailand. Check out places like Hua Hin, Phuket, Krabi, Koh Samui, Hat Yai, Penang, Langkawi, Melaka/Malacca, Terrenganu, Kuching in Sarawak, Kota Kinabalu in Sabah, Borneo, Bali, Lombok, Boracay, Palawan, Cebu. Spend some time in Singapore.
Crete would be mild by European standards but it's still winter and it won't usually be 'warm' like Florida, the Carribean. Not the kind of 'beachy summer weather' you'd be thinking of.
Australia is exceedingly expensive these days thanks to the lackluster exchange rate and strong Australian economy. Great country but not for those on a budget unless you want to stay in hostels. Sydney and Melbourne are wonderful cities but as mentioned above, very expensive.
Thailand is cheap as dirt and has a good infrastructure so internet access won't be much of an issue. Quite a lot to see in the country and it's easy enough to get around. You could rent a small villa on a resort island for not much money.
3-4 months will allow you to see much of SE Asia so you wouldn't have to restrict yourself to Thailand. We loved Malaysian Borneo and Vietnam was quite interesting. Indonesia is a mixed bag, Bali has the infrastructure for working remotely but it's very developed and overrated. The rest of Indonesia is much more interesting but depending on where you go the internet access isn't reliable and there's more hassles to day to day travel or living that may not appeal to you.
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