It's starting to look like my summer is going to be really busy w/ work but I want to spend as much time as I can on the water. If I can stay "connected" working on the water is no problem. Are there internet connections that are more reliable than others and that don't cost a fortune (I once made the mistake of watching 2 movies on a laptop tethered to my cellphone and if I recall correctly it cost me ~ $50). I won't need anything pushing that much data, but I would need to be connected to pick up email, IM, facetime, document sharing, etc.

I feel you on that. I wish I could work from my boat.

My buddy Scott moved his 42 Silverton down to Florida from Michigan after his divorice. He runs his accounting business from the boat the past 5 years.
Being the wifi at the marina sucked most of the time he just used his at and t phone tethered to his PC

2 gigs hi speed but unlimited low speed after that for 45 bucks.

i tether off my smart phone and it is fast and unfailing. Mine is Verizon but i have an old grandfathered unlimited plan ( i use about 30gb a month with no overages). The Verizon service is fast and in the five or six years I've had it i dont think it has ever been down once. The tether app i use is also seamless and has never been down (Easy Tether). My girlfriend has a cap on here plan and I would think if you were just doing work type stuff it would not be to "data intensive" and you'd be able to stay under that 2gb (tho i could be wrong there). Its the social media that sucks up the plan.

I used to tether quite a bit on the water. I have a 6gb plan, and as long as I do not watch a bunch of movies, general office work was never a problem. There are also wifi antennas that are said to extend range to a mile or more. Lots of the cruiser people use them. That might be something to look into if you are not that far from marinas with wifi. This one claims 7.5 mile range. http://www.thewirie.com/

I work on my boat rotating stock in the cooler..

i'm grandfathered into an unlimited data plan w/ t-mobile, last time I activated the teather option they took the unlimited plan away from me (until I terminated tethering and begged to get unlimited back). I'll have to check to see if plans have changed favorably.

I know we have a "jetpack" thru Verizon. It's a mobile hotspot, must work off 4G? Seems to work pretty good.

I've been with T-Mobile since they came to the US 13 years ago. They recently contacted me about changing my plan since I was in an outdated "grandfathered" plan. I thought they were trying to hose me but I heard them out and I ended up getting TRUE unlimited high speed on my phone and my wifes phone for $160 a month total and that includes all taxes and fees. I will never have to pay for overages even if I am roaming and off their network anywhere in the US. Be careful because you can find other carriers offering you "unlimited" plans but they throttle your speeds back after you use up a certain amount of data. For $160 on two phones to have piece of mind that I will never pay a penny more or have to deal with slower data speeds it was a no brainer. My only complaint about T-Mobile is in rural areas their service sucks but now with the unlimited free roaming I don't even have to concern myself with that any longer. IMO T-mobile has by far the fastest and best networks in major cities.

See my post above. Sounds like you and I were in similar old T Mobile plans, they actually reached out to me a couple months ago when I purchased a couple new phones and put me in a great plan, I pay a couple bucks more a month but have true unlimited data including tethering/4G hot spot.