I do recognize the value and potential for great gains in doing a fix and flip and it is definitely on my radar.

The property has about a quarter mile of street access, and no trees or anything to block it, so I wanted to put something there to give a little privacy anyway, and then these trees obviously have to go, so I was hoping to re-use them.

If you can do a renovation loan with 203k or a homestyle loan to house hack a 2-4 unit multi-family, that typically has the highest potential for equity gain with the lowest cost.  

Just make sure only YOU have access to thermostat.5) First understand that leasing is a DIFFICULT job!

We have CDs maturing at the end of the year that could fund a new primary residence.Should we:1) Sell it with no Capital Gains tax.

For the seller (John) to defer capital gains via a 1031 exchange, the sale proceeds must be reinvested into like-kind property within 180 days.

It sounds like you’re in a solid position with your skills, VA loan access, and local handyman expertise.

This can lead to more opportunities and partnerships.Market Understanding: As a property manager, you'll gain a deeper understanding of the local market, which can be invaluable when you start acquiring your own properties.Steady Income Stream: Property management can provide a consistent income, which can be particularly beneficial in the early stages of your real estate venture.Skill Development: You'll develop a range of skills from customer service to maintenance oversight, which are crucial for successful property ownership.Brand Recognition: Establishing a presence as a reliable property management company can boost your reputation, making it easier to attract tenants and investors when you start acquiring properties.Cons:Time Commitment: Property management can be time-consuming, especially if you're dealing with multiple properties or demanding clients.Regulatory Compliance: Staying compliant with local laws and regulations requires diligence and can be complex.Conflict Resolution: Dealing with tenant issues and conflicts is an inevitable part of property management and can sometimes be challenging.Financial Risk: There are financial risks involved, including late payments or damage to properties.Market Fluctuations: The property market can be unpredictable, affecting both rental income and property values.Overall, starting with a property management company can be a smart way to enter the real estate space, especially in an area with a clear need for such services.

From time to time I will hear of people who utilize it well and gain business from it. 

You could point out that since it's a rental for the last 12 years, she will have some serious capital gains to pay with a regular bank-financed sale, and with your proposal, that tax will only come due after the balloon payment.