Libertarians (at least, ones that aren't the anarchist kind) don't believe in freedom. They believe in property rights, which are by definition an encumberance on freedom. (The difference between mere possession and a property right is that the latter is enforced through the government's monopoly on violence.)

This is the argument I usually get into with my more libertarian friends who think property rights and individual freedoms don't impose limits on one another. What happens when someone buys the land all around your house and prevents you from even getting to or leaving your property?

If you buy land where the only access is through another person's private property, that is your own fault. The purchaser has a responsibility to do their own due diligence.

I was thinking more the opposite; You could already own the land and then someone else buys up everything surrounding it.

Obviously, we're leaving LibertarianLand for a moment, but the law generally makes it impossible to split up a parcel of land in such a way that one of the lots will be landlocked. If that lot is going to be landlocked, they must create an easement allowing travel across the property that does have access to the road.

Similarly, easements don't go away when they change buyers. For example, if you own a landlocked property, and you have an easement with your neighbor that allows you to drive across his property on his private road to reach yours, and then the neighbor sells his property, you can still use that road - the new owner cannot say "tough luck."

Well not just that, but also, Uber and Lyft are moving a lot of people around, cheaply, all while providing income for drivers.

All that's going on here is that cabbies made a bad investment and are losing. Sorry, but if you're tying up 90% of your wealth in a single asset, the value of which is 100% dependent on fickle regulation, and you didn't see this coming a few years ago, I don't have much sympathy. No prudent financial adviser would recommend this, and further, if you were so exposed, you should've been paying attention to what's happened in the industry over the past, I don't know, 8 years?

If Uber and Lyft cause the downfall of the taxicab industry, it would probably hurt some people without access to technology or in less serviced areas. But, somehow I think taxi services would rebound if Uber or Lyft started abusing their monopolies.

How can society improve by having less freedom?