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I have been cable free for about 4 years now. The only real drawbacks to me are that I may not be able to watch a sporting event that I want to see, or, much more rarely, there is something I want to see that is only available on cable. Specifically, Game of Thrones. The savings are significant, even if you subscribe to a few individual services. I use both Amazon Prime video and Netflix, and that provides more than enough choices for me at a cost of about $175 a year. I tend to watch a lot of foreign films, art-house films and anime though, so it could be that my needs and the choices available are better suited than for most people. I could probably do without Amazon, to be honest, but it does offer some additional choices Netflix does not, plus it gets me free 2 day shipping when I order from Amazon, which is nice. I went without Netflix for a while, but I went back and they really are the best if you could have only one streaming service. The quality of the video is also consistently better on Netflix if you have a slower connection.
I have a couple different devices I could use with my TV. What I use for much of my viewing is my old Wii in my basement and a Wii U in my main living room. It is easy; there really were no headaches, and you can use the same account on multiple devices. I considered getting a Roku, but I already had a Wii and decided it would be an unnecessary expense, which defeats the purpose of being frugal by cutting the cord. The regular Wii only supports 480p though. Also, don’t underestimate the amount of HD content you can get over the air. I get 14 channels with an antenna, which includes all the major networks.
Despite minor shortcomings, I don’t regret “cord cutting” at all. I save over $800 a year and get to see 99% of what I want. For those football games that I just can’t miss, that pays for quite a few pitchers down at the local sports bar.