Assume for the sake of this conversation that all of my other finances are in order.

I would not converse with tenant in any format, as things could end up in court, if he declines to leave and has to be evicted etc. also don't confront in person, you said he is MMA fighter, good rules to live by include : Never get involved in a land war in Asia , and never anger a man with Cauliflower ears.

Looking for advice on how to maximize tax benefits on an upcoming conversion of my primary home to a long term rental (temporarily).

It helps to have a conversation with a lender in advance (if you are serious...don't waste anyones time) to explain your situation and see if there are any red flags.For single family or 4 units and under a pre approval is also not needed but does go along way. 

I am happy to have a conversation.

How much work needs to be done in the basement conversion?

Not many on BP will have gotten there with no debt.But, conversely, many who are or have been retired choose to pay all debt off.There’s an approach to get you going, and an approach to feel confident in early retirement.Many investors who dont know what that inflection point is will continually leverage thirsting for more, and ultimately wish they’d listened to Dave.

Conversely, if things don't go your way...you run into mold or some other unexpected issue, the real estate market takes an unexpected negative turn, a terrorist runs airplanes into a NY skyscraper...things can go South quickly for you and your family.

Here are a few reasons I want to move into this industry: I love property (and would love to own it around the world), I enjoy spending time with family and traveling, I want a more flexible life down the line so I can spend more time doing the things which are important to me.I am looking for someone in the UK or European market and would like to have a stimulating conversation with you to learn more, and I would love to offer my time and energy to help you towards your business.

Agreed, I had this exact conversation with another investor today when they brought up the lower purchase prices in small-town Minnesota.