Advantages of buying property in Oak Bluffs, Massachusetts include:

1. Proximity to the water: Oak Bluffs is nestled on the eastern shore of Martha's Vineyard and has several beaches that are perfect for swimming, fishing, and other water activities.
2. Stable real estate market: The Oak Bluffs market has experienced steady growth in recent years, which is a good sign for potential buyers.
3. Strong sense of community: Oak Bluffs is known for its tight-knit community, which can make it a great place to live year-round or as a seasonal resident.
4. Rich history: Oak Bluffs is home to some of the oldest and most iconic architecture on Martha's Vineyard, including the gingerbread cottages in the Oak Bluffs Campground.

Disadvantages of buying property in Oak Bluffs, Massachusetts include:

1. High cost of living: Like most cities on Martha's Vineyard, Oak Bluffs has a higher cost of living compared to many other parts of the United States. Housing, groceries, and utilities are all more expensive than average.
2. Seasonality: As a popular vacation spot, Oak Bluffs can feel empty and isolated during the non-summer months, which may not suit everyone.
3. Limited job opportunities: Oak Bluffs and other towns on Martha's Vineyard have a limited job market, which may require buyers to commute to other parts of Massachusetts.
4. Natural disasters: Oak Bluffs is vulnerable to hurricanes, flooding, and other natural disasters, which can impact property values and pose a risk to homeowners. However, it is important to note that Oak Bluffs has highly professionalized emergency management services, which mitigate the risks of natural disasters.