Hi John - Under the passive activity loss (PAL) rules, you can deduct rental losses against passive income. 

It was our primary a few years ago and we decided to sell so we could escape the capital gains tax.

If you have lived in the property for two out of the previous five years you could qualify for the 121 exclusion, where you get the first $250k ($500k if married) of the gain tax free.

Trying to bend the rules will always come back to get you and could end up costing you more at the end of the day than any benefits you gain from it.

What education should i gain before purchasing my first rental property?

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. 

Pull it out over the next 5 to 10 years as you gain REI experience.  

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.

That’s a hefty loss, which, as passive income you cannot even take against your W2 income.Can you make it a short term rental?

You may choose to invest in real estate directly by acquiring a property, or passively by investing through a syndication (or by being a lender to someone else.  2) pencil out the numbers to see if the math is in your favor for a Roth Conversion and real estate investment with a SDIRA.