Last but not least....A few members in replies have already mentioned why it makes sense to hold…….I very much appreciate ALL FEEDBACK, however I think it will be helpful to provide some added context as to why I am absolutely certain (and my CPA’s are convinced as well) on my decision to liquidate the entire portfolio and onceAs I educate clients on daily, income tax brackets as well as long term capital gain tax brackets in our country are more favorable right now than they've been at any point in the past 80 years.

I had a local bank provide a 1031 without fees. 

If you need an insurance agent who can look into it for you and provide you with some quotes, reach out. 

Happy to connect and provide some feedback if interested.

There are some public sources (www.city-data.com) that can provide good baseline information.

You manage the headache of guests and communication, cleaning, etc. and he provides the property, but shares in the expenses and profits.

Sometimes making a smaller profit and providing value is far better than holding out for a bigger payday on a bad deal, I like that.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

Travel nurses are making bank and sometimes I think the locums companies provide lodging.

The great thing about living in a high cost of living area is that your salary / wages are hopefully also very high.If you are a new college grad, I would focus the next 1-3 years on increasing your salary as much as possible(gain new skills, new certifications, change employers, etc).Once you make more money, you can easily get in a position to buy a property on a more frequent basis.Best of luck!