I had a conversation just a few weeks ago with an agent I know that had a property listed as a single family.

Usually I call about a property, ask a few closed ended questions and the conversation ends there. 

I would start the conversation with questions like "what are you looking to lend on?"

So as you guessed from the title - I bought Home in Largo FL with an unpermitted garage conversion.

If you’re interested in learning more about becoming a featured agent or know someone who’s interested, just send me a message and we can start a conversation to see if it would be a fit for you.

Which is a great thing - I'd break it down like this:How much money besides DP - These are important conversations to have with your broker/lender.

What’s worked well for me in the past is simply having a conversation with the tenant.

Best advice - learn as much as you can about subject to transactions (both good and bad) and then have a good open conversation with your friend and you can both make an informed decision together.  

I am currently looking at purchasing a SFH with the intention of turning it into a top/bottom duplex and here's why:1. I have already talked to the city and they are fully on board and are excited to see more housing ...

If you want to remain friends with this old buddy and not go another 15 years with out seeing him I would just let normal conversation happen about each others work and personal life, and when he is ready to jump into ownership he may or may not request your input or assistance.