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I pretty much do this already with my 17" laptop often working from friend's places since all my friends have wifi in their homes.
My laptop supports two screens so I could carry a LCD flat screen too if I wanted but most of my friends have an extra monitor that I plug into when I'm over at their place since I prefer to work with two screens.
As far as getting internet access at hotels you have lots of choices plus many coffee shops have internet access.
T-mobile is the largest wifi provider. They are in many coffee shops and some hotels. Their service costs $30 per month unless you also use their cell service and then it is $20 per month. Best Western hotels have free wifi access as do some other hotels. The thing to do is settle on one wifi provider and then stay in hotels that offer that provider otherwise you end up paying for many providers.
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