Start with a few basic questions --- Do I need/want to change residences? What do I require in an residence? What might I want/need in the future?
These considerations will vary with each individual/couple ... but can help guide your decision making
A tool to use is writing considerations like these on business cards, and sequencing them according to your priorities.
Environment
how close to "town" (library, shopping, coffee shop, theater)
how close to the "woods" (walks, birds, critters, water, ...)
how close to transportation (airport, bus/..., freeways -- transportation provided by community)
how close to friends and relations?
access to recreation/Activities - skiing, water, ocean, theater, life long learning
Proximity to your medical care - Doctors, dentists, pharmacy, specialists, etc.
Proximity to groups with which you are involved? Church, clubs, OLLI, etc.
Comfort in the climate, neighborhood, etc.
Facilities
Importance of community, or avoiding isolation
Proximity to neighbors
Average age of folks in community (do they do things you want to do?)
shared facilities - meeting space, theater, exercise, pool, workshops, gardens
"intentional" community -- designed to bring residents together?
Security - at outer doors, onsite staff, cameras, other
walk to dining options
garage, car port, storage, special storage (boat, kayak, ..)
exclusions - Pets (dogs, cats, other), age specific (55+), non-smoking, ??
Facility wide services - snow removal, external maintenance
life-planning -- accessibility, proximity to medical services, in-home options, assisted living, nursing care
personal services - meals, laundry, cleaning,
Continuing care - assisted living, nursing care, memory care, other?
How does it relate to impact on your family, possible care-givers, etc?
Financial variations
Up front costs (buy-in, entrance fees, long term care insurance, ...) -- and possible return of all/part in specific time frames
(NH residential communities requiring significant up front fees are registered with the NH Insurance Commissioner)
Monthly costs (rent, condo fees, utilities, Internet )
Expected changes in costs (taxes, condo-fees, rent, maintenance) -- and what control do you have over these?
Implications of your life style options? Travel,
Taxes - State, property, etc. -- some fees may be tax deductible
(property tax, prepaid health care in some CCRC's etc.)
how does this choice play into your estate planning?
How long do you expect to live? -- and what happens if you live much longer? (Some facilities have "Beneficence Clauses" to assure continuing use)
External factors and the future
Climate change -- impact of rising water, stronger storms, greater variations .
Tax changes (national, local) how they might impact costs, deductions
Health care law changes \
Social Security, Medicare, Medicaid