Option 1:  Spend $50,000 on a conversion from a huge basement garage to a mother-in-law unit that would increase your rent by $500 per month on an existing rental.Option 2:  Spend $50,000 on a down payment on your next deal that should cashflow $200 per month after expenses, in addition to the loan paydown, appreciation, and tax benefits.

After many conversations I guess Private insurance normal there.

Buying the right property knowing you could do some conversion could be a big win it seemsz I wonder if permitting or some other red tape would get in the way if you specifically targeted This kind of situation for value add. 

The one item we fudged up on are the appliances.

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I am sorry that this message was so long but I want you to succeed and I had a bit to say to inform you.Feel free to ask me about any other particular items that need more attention and you think I might be able to answer. 

Maybe a nice little gift basket with some useful items.

Get item out of pawn and then have to do it again to eat.

"How you doing, your family member is selling me the roof over your head and you need to leave" doesn't seem like a good conversation starter.Lastly, is there an industry standard incentive that typically works to motivate "tenants" to move out sooner than later?

I would use 50% to stay conversative.