Although I have not yet purchased my first tax deed property, I have been spending a considerable amount of time researching the tax deed sale process and the tools that can be used to streamline the process as much as possible- one of those tools being PropertyOnion.com.The website seems to provide a wealth of knowledge for pretty much any property you'd like to research, and provides data that could be useful to a variety of RE investors.

If you can stomach that initial phase you'll be in a great position when the property is cashflow positive and worth considerably more. 

Also, for your consideration, instead of cashing out the annuities, can you use them as a collateral for future loans?

My current agent is part-time...a consideration that I didn't mention in my original post.

Holding onto a property merely for tax considerations is a dangerous gamble.But if you want to gamble - yes, selling in a year without a W2 job usually saves on taxes.

Or any other considerations I need to be aware of?

Like they both mentioned, there is some amount of consideration for your life and family.

As I’m not very familiar with the US market, I’m doing my own due diligence.Any thoughts or advice on these markets or others I should consider as well as any other considerations? 

Great time to explore ADU's considereing recent legislature: https://www.mass.gov/info-details/accessory-dwelling-unitsWould love to connect!

--Feel free to share your own thoughts and considerations when you're looking for assistance from a PML!