The reason I'm interested in buy & hold is because I have a really great job and my goal is to simply supplement my income both now and in retirement.

But I did not get a supplemental tax bill, so all was well.So, I can absolutely guarantee that a Trust will NOT save you from this new proposition. 

Grow your career and income, max the 401k, then consider the real estate to supplement it.

We brought in a small supplemental refrigerator for our tenant. 

@Jon ReedWell said, and I agree with most of your reply on the thread - except the part about moving your holdings into bonds.Selling off a portfolio is tricky, cap gain rates are brutal, and if you are a 60 year old investor with good cash flowing rentals that supplement a retirement, why not just keep them and work to develop a tax minimization strategy, and who knows maybe you will live to be 90!

They run out of cash and they can't take care of their rental properties.If you have no cash, goal #1 is to get the cash.Wholesale, or fix-n-flip houses...or even being a real estate agent first so that you can sell houses to supplement your income and accumulate cash...or just (and combine it with) save money by being wise in spending it.In parallel to accumulating cash, you can accumulate knowledge and network so you can find the right people who can help you accomplish your goals.These 3 things are what I did when I lost everything back in 2002-2003.

The reality is that with only one unit rented, you are going to be supplementing the cost on this quad more than just the value of the rent in the unit you are occupying. 

I currently work a full time 9-5 and I hope to supplement some income on the side and maybe use this as a future retirement option.

I understand why the PM was defensive, anyone would be when your professional license could potentially be at stake, and my apologies for implying that the PM overreacted.Also, thank you for your response I did not think anyone would so it's very comforting that you took the time to write.There must exist some type of service where though the PM performs most of the managerial duty, there is a "supplemental" manager who is also entitled to fees.When you have a rental home where the rent includes fees for landscaping, obviously a piece of rent goes to landscapers, yet landscapers are not licensed real estate agents, so how does that work legally?

Two points - have you considered supplemental medical insurance like medical gap insurance or medical indemnity insurance?