It’s been incredibly difficult to see this situation unfold, especially given how much work and sacrifice went into saving for these properties.

If have investment property, we are looking for relatively updated units (we are ok doing some work ourselves), class C+/B tenants, with rents either close to market rate or that can be increased.

I understand it become tad difficult to refinance since some lenders wouldn't lend on the home in trust, but is it easy to sell a home in a trust, just like you are buying in a trust?

I'd happily accept the former, though the 16% YOY property tax increase would be a non-starter for me.

Purchase price: $250,000 Cash invested: $14,000 I purchased and managed a rental property in Chicago, focusing on strategic improvements and tenant satisfaction to increase both its value and profitability.

In my area these are rare so they are difficult to set market rent, and I imagine get a lot of wear and tear with a lot of occupants living there. 

This could significantly increase the sale price and net profit after selling.Pros of Selling: Immediate large cash flow that could be reinvested elsewhere (stocks, other real estate).

More difficult question that was not asked is do you get rid of these tenants property and I think that is as easy a question.  

, but very difficult to DIY remote manage.

Similarly, quality dividend-paying companies often retain some earnings to reinvest in their business, increasing the company's (and your) value over time.