HELOCs or traditional financing may also be better options to preserve retirement funds while minimizing immediate tax liabilities.This post does not create a CPA-Client relationship.

Overall, my primary goal is to create the opportunity to get into another home at minimal cost while keeping my parents in the current home, so I'm leaning toward transferring/selling the current property to them.

And while that number varies somewhat, the most common number of different issues that minimizes risk is 21.  

The average rental home price I am looking at is between $175K and $250K for a 3 bedroom house that requires minimal work in a nice neighborhood. 

Any law that tries to do otherwise conflicts with sb13 and ab2533 (unless the unpermitted units was created post dates of protection by those laws).i agree he should get it permitted especially if close to the price quoted, but issues due to unpermitted units that are protected be sb13 and/or ab2533 present minimal risk and if it does happen get HCD to assist in any issues. 

K-1 losses, generated through depreciation and cost segregation, can often offset distributions during the hold period, minimizing taxable income.

A property in Boston will appreciate well, but with minimal cashflow.

For the past 3 years, I've paid my property manager in Costa Rica via paypal, a minimal cost for me and he gets his money next day.   

See if the Seller will finance with a minimal downpayment.2.

Having the ability to live for free, while minimizing the taxes on my W2 income.