You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

This strategy allows them to eventually exclude up to 250,000 (500,000 if married filing jointly) of gain from taxes when they sell the property as a primary residence.Hope this helps!

Might have to do a joint venture. 

As far as your primary residence, if you have lived in it 2 out of the last 5 years, you should not have to pay taxes on capital gains (difference between what you paid for it & what you sold it for) up to $250,000 if you file your taxes as an individual and $500,000 if you file jointly with a spouse.Just a disclaimer, I am not a tax professional.

Any tips on managing joint ownership or deciding to hold or sell would be greatly appreciated. 

I would get an attorney or title company involved to create your loan documents to ensure they comply with the law and cover all the aspects you need.Another method that is likely your best bet to take on investors is to create a joint venture (JV).

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I file jointly with my wife who's a w2 employee.

., adding rooms, bathrooms)-Cosmetic Enhancements-Eliminate Health and Safety Hazards-Energy Efficiency Improvements-Major Landscaping (e.g., grading, tree removal, adding walkways)Non-Acceptable Renovations:-Luxury Items-Commercial Use-Temporary Structures-Non-Residential BuildingsBoth of these renovation loans are similar in many ways, but the key differences are:1.

Here is a solid example you can adapt for a joint venture (there are differences, beyond just nomenclature, for a partnership and a joint venture): https://templatelab.com/joint-venture-agreement/Again, I would caution use of this document without a professional to review it.