Remember, everyone else’ is either not bidding or bidding less because of this situation, this is a plus to you, not a negative. 

I asked my CPA to sit down and go over the math and the pros and cons for my specific situation and portfolio.

And that’s another discussion.Allow me to requalify the answer into a set of questions: Are you a person who likes to have insight into their tax situation, optimize their tax footprint, and do not shy from tax concepts?

The value of the trailer is so low and the title is lost that no one wants to deal with it, everyone is worried how much it will take to demolish and remove.My background plays a role in my situation, I've been in construction for twenty years and know I can fix this house for little cost (5-7K). 

I hope this helps get your situation on the right track and gets the conversation going with your accountant.

While my situation is relatively straightforward with a W-2 job and 5 rental properties, I feel I'm not receiving the proactive planning and guidance I seek.

Given your situation, here are some considerations and potential steps:If you plan to convert your current residence into a single-family rental (SFR), you may want to explore refinancing options.

You do not always have to go the attorney route it really depends on your situation and what you are trying to accomplish.   

Paul - you’ll want to get a lawyer to create a  new lease that provides necessary coverage or at minimum an addendum for sub-lease/arbitrage situation.

Though in this situation I wasn't planning a renovation until April of 2024.