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Hi, I am interested to purchase the above at the 20k max price ranges. Can you please advise me regarding the different models and what to watch for? My family would be doing some road and beach trips for the next coming months. Moreover, I have noticed that the Freelander tends to be cheaper than the other rovers? Why is that? does it have a different platform? I have heard a buzz also that one time the Ford Escape's platform was also same in one of Land Rover's models. Is that true? Thanks for all your replies.

It really depends on what you need in a vehicle. In this price range, almost any Land Rover/Range Rover model you choose will be high risk, reliability-wise.
Freelander is a much smaller model than all the others, was less expensive when new, generally had less powerful and smaller engines. Early Freelanders (particularly with Rover's K Series or KV6 engines) had poor reputations for reliability and were prone to overheating.
Early Freelanders were developed when BMW owned Rover, the later Freelander II came at the end of Ford's ownership of the brand. Now (of course), ownership has changed again, with Indian Tata group owning Land Rover.
Although there is all sorts of speculation about Ford Escape/Mazda Tribute and even Honda CRV platform sharing, my understanding is that the Freelander shared platforms with none of these vehicles. The Freelander II shared some undepinnings with the Ford Mondeo.
If you really want a Land Rover in this price range (and I'm not sure that I would), perhaps a Discovery II TD5 or a Freelander with the BMW diesel engine might be OK.
Have you considered other brands. Toyota, Nissan and other Japanese models would offer much better reliability.