I'm a Realtor who was born and raised in Hampshire County with family still residing there, so I'm familiar with the area.
As Paul has already said, usually condo fees are paid monthly.
Regarding tax breaks for Over 65, there is something called a Circuit Breaker Credit. Here's a link to more information on the subject: http://www.mass.gov/?pageID=dorterminal&L=6&L0=Home&L1=Individuals+and+Families&L2=Personal+Income+Tax&L3=Current+Year+Tax+Information&L4=Guide+to+Personal+Income+Tax&L5=Credits&sid=Ador&b=terminalcontent&f=dor_help_guides_abate_amend_personal_issues_realestate&csid=Ado
If you need any further assistance feel free to contact me via http://www.elizabethherbert.com.