Hey @Johnny Smith, ask your CPA how you would be able to apply losses to your W2 to get the conversation going.

It's not conversational.

My initial protege also had one (garage conversion) a few years ago that was not hands off that received a pathetic appraisal.  

How has the conversation moved along?

Trying to narrow down which strategy will best suit our goals and lifestyle is my current focus, and I am looking forward to having meaningful conversations here on these forums.

Once you do this conversion it will be difficult to change it back to a traditional long-term rental. 

I had a conversation with one of my investors yesterday and he was asking where is all the positive cash flow and the equity appreciation on our deals? 

I would also be super conversative on spending.

Always get permits for conversions and be cognizant of the experience renters will have in your home.

There’s a huge difference between winging it and setting up a system that consistently brings in genuinely motivated sellers.Get a website, focus on the 3 pillars of conversion (look it up), and crush it.