Some more thoughts after reviewing this thread again.
Connect to VPN - remote to my computer in the office and work away. We have a couple of people in my position who are 100% remote.
In general I'm a believer that technology should support the way people work. Sometimes technology becomes an end in itself and a philosophical reset is appropriate.
There are very few applications that require RDP (desktop and server admin support for Windows and Mac are exceptions). It took me years to wean my wife off GoToMyPC. The last new computer was a high power laptop and a docking station. Now she can work with or without an Internet connection, and slow or intermittent Internet connection is no longer a source of frustration.
Now PsychedChicken may work for an employer whose IT people are not rational. *grin* RDP may be the only way they support remote workers. If they have configuration management and backup concerns those can be addressed.
OS and application update policies are another factor you will have to come to agreement with your IT people about. You need to be compliant with their policies and they need to understand that you may need a day or so from time to time to accommodate a massive download.
We have the Bullet/Bad Boy antenna radio. It works great if we can get an access point ashore. THAT is the problem, down here in the Caribbean. Even the pay access points can be poor to terrible and much of the time there just isn't one at all while you cruise the islands.
Your experience is common. That is why most people have multiple Internet access mechanisms.
WiFi access is so often dependent on a lot of moving parts that are not professionally designed or implemented. Inadequate or unreliable backhaul is the biggest problem in the islands. When you can get a good connection it is cheapest and fastest of the options.
Interestingly, cellular is getting better and better in third world paradise. Cellular is often the only means of communication for locals so there is a lot of pressure on companies and regulators to get it right. I generally get better performance in most of the Bahamas than on the ICW in NC for example.
In the Eastern Caribbean there are some good places with coverage holes in between. Again if you can get off bandwidth intensive applications like RDP and focus on transferring real data and not desktop refreshes you'll be happier and more productive in more places.
As for offshore sailing, if you've got the bucks I'm sure it can be managed, but the only vessels I know that can manage it for commercial purposes are those with over 100k in those huge dome antennas and vessels valued well over several million bucks. The mega yacht crowd have no problem connecting to the internet anytime, anywhere.
I was proposal manager for a $100M effort while I was crossing the Atlantic in 2006. It took some adjustment and planning and organization ahead of time. It helped that my boss was a sailor and his boss was a boater and both thought what I was doing was really cool. The team felt engaged since my daily all-hands email included a little insight into life at sea. We were able to make everyone feel engaged and part of something special. It helped that my company was supportive and used to working across multiple time zones and countries. It also helped that we ultimately won the bid. *grin*
The workhorse communication went over HF/SSB Pactor with Sailmail and ShipCom. Slow but reliable. In England, the Azores, Bermuda, and Norfolk we arranged for a few days of really solid high-speed Internet and lots of conference calls. That was not inexpensive but not terrible.
I also am looking for a solution to this problem that won't break the bank. Let me know if you find it.
Today, on the same boat, I have more diverse options. I still depend on HF/SSB for long range communications ($250/yr for Sailmail, free through Winlink). I have both a Ubiquiti Bullet and a RedPort Halo for WiFi. The only reason I have both is I sell the things and I drink my own Kool-Aid. I also have a cellular modem that distributes connection through WiFi inside the boat. I now have a Globalstar satellite phone that I am experimenting with; it is a prototype product so as long as I'm part of the evaluation I don't have any costs. At my usage level the data costs would be about $800/yr.
Cellular hot spot works well in southern NE and I am able to work on my laptop and use the net. But it is consuming data allowances.
How well cellular works from you boat depends on a lot of things. Between topography and antenna pattern tuning by the service providers the Atlantic ICW in NC and GA are really poor for example.
"Cheap" is relative. If you just want to stay connected the costs are extra to your life. If you need to stay connected for work those costs are part of doing business and you have to fit them into your budget.
My cellular bill for a smart phone and a separate cellular modem runs about $125/mon from AT&T.
I got an Island Time system a couple of months ago and am traveling down the east coast. I haven't been very impressed. The system seems to bog down to the point I give up and make a cell phone hot spot, which works well but eats data.
You may have a hardware problem, an installation problem, a configuration problem, a training problem, or a problem with expectations. Have you called Bob Stewart and talked it over with him? His customer service is outstanding.
I had the Verizon hotspot for a year.
Verizon coverage is darn good in the US. Hardware and service cost to get multi-mode connections outside the US really adds up. A GSM phone or modem (AT&T or T-Mobile) makes your life much easier in the Bahamas and the Caribbean (and Europe and most of Asia and the South Pacific). Between AT&T and local SIM cards and a Google Voice (GV) account my gear just works almost everywhere. GV solves the consistent phone number problem.
Still hope KVH comes out with a cruisers package. Can't afford them or the Verizon plan for any length of time.
They have. It's still expensive.
I have a presentation on this material I've given a number of times for SSCA, SSU, BoatUS, and boat shows. If there is interest I can do a Google Hangout presentation for SailNet.