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The "bailiff" is not the same in British (Irish :-)) and American English. In this use, the bailiff is the person / firm which executes writs and orders, for example about debtors. The bailiff may be in charge of repossession or eviction. In the US this could be done by a marshal or sheriff, less often (and usually not in the case of real estate) by a collection agency.

The visit of a bailiff to assess the value of the land should be seen as the first step in the process of selling the land and evicting the squatters. They may decide to evict the squatters beforehand to facilitate the sale of the property.