At a minimum, I recommend selling it within three years of renting it so you don't lose the tax free gain on sale of a primary residence.

My and Wife special in this area, we have tons of free content on our Page and our YouTube on the options you mention, and we try and cover the good and bad of each.

For joint owners who are not married, up to $250,000 of gain is tax free for each qualifying owner.If your spouse dies and you subsequently sell your home, you qualify for the $500,000 exclusion if the sale occurs within two years after the date of death and the other requirements discussed above were met immediately before the date of death.Good Investing...

Feel free to reach out with questions!

I am interested in buy and hold deals to generate a large amount of passive income so that I can angel invest and be financially free.

Tax free.

I'm new to having an STR and dynamic pricing tools and just tried a Price Labs free trial for a few days.

Also, you don't want to lose the tax free gain on sale. 

If so, I would definitely try to wholesale, unless there are active properties in the area with the same ROI.Feel free to send me the details, I can analyze it and give you feedback on it. 

If you have any recommendations for a GC or management company, feel free to send them my way or just send a message to say hello!