In the New Haven area there are a number of condominium communities catering exclusively to over-55ers. These communities offer a step up in the quality of life of such adults: they offer sensible home architecture, maintenance-free park-like grounds, and community amenities (eg. gardens, recreational facilities) far beyond what most typical homes offer. Above all, these communities often offer -with unsurpassed convenience- a social environment (through both their formal programs and their informal settings) that contributes immensely to the well-being of the residents.
With the population aging and the over-55 demographic wealthier and more demanding than in generations past, I suggest that these "Active Adult" condominium communities are bound to grow in popularity. I suggest that you look into such condominium communities in the New Haven area, focusing on active adult condominium communities close to town centers and within close proximity to libraries, senior centers, restaurants, professional/medical offices. I am quite familiar with two such communities in Hamden: The Commons at Mill River and The Summit at Hamden Hills.
I encourage you to consider what I've written here, look into these two communities, and refer to realtor.com for properties listed for sale at both the Commons and the Summit.
Wishing you the best,
You have asked a lot of great questions that an investor should be asking. However, there is no short answer. Nobody can tell you which complex will be hot in the future, all we can do is look at what has happened historically.
If you are serious about investing, it is very important to start out right. You should pick a Realtor to build a relationship with that you can discuss your investing goals (both short and long term), your strengths and weaknesses, and together, find the properties that work for you. There is no magic formula, but working together you have the best chance of success.
The other thing that will help you is networking with other like minded people. The easiest way to do that is to join a local REIA (Real Estate Investors Association). As an investor, I am a member of 3 different ones and have gained a great deal of knowledge from them.
If you would like to contact me to talk about how I might be able to help you further your investing career, please contact me at (860) 736-1002 or firstname.lastname@example.org .