This would also suggest that massachusetts is a title theory state because legal title is held by a trustee not the "owner" aka person in possession of the property.

Agree.If there is damage by a tenant (smoking, candle wax, crayon, etc), it's on them, but normally it is wear and tear for the landlord to cover.The first thing we do when we take possession of a unit is assess whether painting is needed, and full or partial.

You are (considering) buying a property and intend to receive the benefits of ownership (possession) as bargained for. 

Then I filed for possession.

The property is being sold subject to: All taxes due the municipality not foreclosed by this action, Water and sewer use charges not foreclosed by this action, All building and zoning regulations of the municipality which affect this property, All building lines, easements, restrictions and all other matters concerning this property which appear of record, The rights of any person in possession or occupancy of the property who have not been made parties to this foreclosure action, The right of the United States of America to redeem the property, if applicable under Federal law, Any other liens on this property which have not been foreclosed by this action.

Under Georgia law, if a tenant has actually abandoned the property then you do not need to obtain a writ of possession.

Pursuant to a written lease (the "lease") dated xxxxx, you are a tenant for the premises described as xxxxxxx (The "Premises"), of which you now hold possession. 2.

Actually, An eviction is a suit for possession of the property and in no way would an HOA has standing to sue for possession of your property 

I saw some of the properties with status "Occupied", "It's unlawful to disturb the current occupants" and "Buyer is responsible to obtain possession of the property" . 

The divorce gave your mother POSSESSION , but may or may not have also addressed OWNERSHIP.It also depends on the current type of deed recorded on the property.