I like to use AI when communicating with sellers/agents to keep an up beat tone to the conversation.

I also agree that a garage conversion will cost much more.

How has the conversation moved along?

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

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.

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.

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

As others have mentioned you could have a conversation with your tenant(s) about splitting the cost.

Ive certainly purchased properties at serious discounts to the listing price....but it wasnt just random shotgunning of the offers.What I usually start with when trying to see if a lowball offer is appropriate is having a conversation with the listing agent first.