I didn't do gray areas on my taxes, but when I sold out and retired. I sure was glad when I hit the 3 year mark, then the 5 year mark and finally the 7 year mark. Any chance for a audit are now in my rear view mirror. Taxes are so simple with only social security and interest income.
Over 30 years of owning trucks, I tried staying away from the gray areas. But every time there was a letter from the IRS my heart would stop. I never went thru an audit, I can only imagine what that stress would be like. Stress is the main reason I finally sold out, remember stress is the silent killer.