Karin,I know I’m a bit late to this post, but I’d like to offer some advice for your future investments.

The investor wants me to come up with a few options for how we can partner on a future deal (coliving home in the Cleveland market).

I will definitely take you up on the chance to chat more in the future.

Most importantly, I'm sure you would agree, this has been a huge learning experience that will allow you to be a more successful & savvy investor in the future based on this experience. 

Tyler local, so sparked my interest whenever I see anyone post about the area.Given that your duplex is fully paid off and generating a steady cash flow of $1400 per month, it's understandable that you're having second thoughts about selling it.

The additional cash you have due to leverage put into more hard assets and the cash flow generated put into fixed income/equities after reserves.

Not to say you can't get a property manager in the future but I think it's best to learn the ropes first. 

However, you can defer taxes under §1033 involuntary conversion if you elect to reinvest the proceeds into a similar rental property within two years (three years if the government condemns the property or threatens to do so, and four years for a principal residence in a federally declared disaster area).To reduce taxable gain, consider:Electing §1033 treatment and reinvesting the full $300K into a new rental property to defer taxes completely.Partial reinvestment, where only the portion not reinvested is taxable.Properly documenting all replacement costs and property details to ensure IRS compliance.Using cost segregation on the new property to accelerate depreciation and offset future taxable income.Since the §1033 election must be made, consult a tax professional to ensure compliance and maximize deferral benefits.This post does not create a CPA-Client relationship.

The only members I've found with multiple deals are his partners who were already successful, just like Pace, and they use the newbies to help generate more deals.

I'm not sure I would get to cute trying to squeeze every time out of it now with a lease that might cause you issues in the future, but the scenario you describe is common and probably smart.