Selling to a family member (or transferring to a trust?)

[Eugene Lubman]

Hi,

I am planning to sell my 3-unit investment property to my parents.  The idea is to provide them with a steady passive income in their retirement.  I will still be managing the property, as well as be an inheritor, so ideally my name should remain on the title.  The property currently has a mortgage on  it, but it should be paid off during the sale as my parents want to own the property free and clear.  Or is it better to transfer the property to a trust owned by my parents where I will be the beneficiary?  Also, I will probably want to do a 1031 exchange as I am planning to buy another investment property to replace this one.   I will almost certainly need an attorney, but I am not even sure where to begin.  What is the most pain free (and, ideally, tax-free) way to accomplish this?

Here are my initial questions:

1. Should I be looking for a tax attorney, a real estate attorney, or a trust/estate attorney?

2. The property is in Connecticut, I live in Massachusetts and my parents are in New York.  What state should the attorney be licensed in?

3. Given that my parents are elderly, what are the pros and cons of selling it to them vs transferring to a trust?

Thank you.

Gene