If your value and rents go up over time then you come out financial far ahead of the person that succumbed to the trap of "financial security means collecting rental income from a free and clear asset."

I would submit your current cma with your counter offer, and make it clear that is what you are willing to pay in the current market.

I think there's a clear difference between being "friends" and "being friendly.' 

I have to say that I don't yet have a clear number yet as far as what I can actually charge for rent..so it might be higher than I am assuming. 

Once he is in the clear, there will be more options.  

Just make sure the clause is clear in your lease because when/if it breaks or needs to be repaired they will definitely ask you to fix or replace.

I couldn't get any clear hard and fast rules but if it's 6 stories and below, depending on the year built, it's probably wood frame.

Most California investors make money on appreciation rather than cash flow, even when a property is owned free and clear.

We BRRRR the properties (or hold them free & clear, depending on investor's preference), return the invested capital and split any excess in the refi 50/50.

Just leave really clear instructions on head use!