You want to consider regions that you are personally attracted to first.

Note investing is something I hope to get into the future, get an attractive return and not having to deal with tenants.

North NJ is very attractive for many reasons, one of them is its convenient transportation to the NYC. 

You therefore have to research well on the market before you consider this kind of investment that requires town location without too high prices but attractive earnings at any given time.Cities such as Dallas-Forth Worth, Charlotte, Indianapolis, and Atlanta have varied job prospects and available affordable multifamily properties.

This classic “leveraged buyout” is the basis for what we call “private equity” (KKR) today, but of course requires significant capital, business and financial expertise and experience, and a business target large enough to attract top tier management with incentives to out perform the previous management.   

The auction can be competitive but if an investor is willing to put in the work and jump through the necessary hoops, there are attractive investment opportunities each month, including the opportunity to buy single family houses for less than $10,000.

For properties that I know will attract many investors, I explain wholesaling to seller at listing, that they are likely to be inundated if they don't limit it, and then have seller state in writing, up front, that I should not send them anything under a certain price or with certain terms like fully assignable.

How would I go about analyzing, building, financing a project to attract well healed boomers?  

It is the properties which are intended to attract a high number and quality of tenant so you can try to pick the best one. 

Along with a vibrant art scene, restaurants & easy walking it attracts year-round visitors seeking fly fishing, white water rafting, kayaking, skiing & snowboarding that is off the beaten path..