And of course, age of building matters too.  

More regionally, Boston's STR regulations have gotten more stringent, moving from earlier proposals that would have allowed out of state rentals, to its current form allowing only home share or owner-adjacent rentals. 

If you're interested in the Coachella Valley you can also consider 55+ communities if you are of age.

Meaning I won t be using my 401K like many at the age of 65+...

We do have other investments in the market with our non-taxable assets (401K) which we plan to use post retirement age (60).

Mario,Discuss with the agents the specifics on the property (ie age of roofs and systems, claim info, pets, pool, etc.) before making any changes. 

Both to maximize profits (two rents) and incase we need to use the property to care for aging parents in the future. 

If you are more focused on building wealth and enjoying the benefits at the traditional retirement age, you should choose a different path.

Tough to find lenders if the loan amount is less than $100k.I specialized in c class houses for condition (age) vs c class rough neighborhoods.  

In this day and age it has to be a necessity!