IMO is always pays to be nice, respectful and to always start the conversation out with (who you are, what your doing and then what you want).I am dumbfounded by the statement that title searches conducted prior to a sale do not reveal all outstanding bill/liens/tax/whatever. 

What I took away from the conversation was that more seasoning might allow them to justify a higher ARV.

I document everything, every conversation with a tenant or repair person.  

The 'fix' is conversion, but that takes a lot of votes in favor of condo termination and a suitor willing to wait if you don't get full buy-in.

J Scott opinion also helps with the hard number conversation. 

May be worth starting a conversation to see if you could do a conditional sale where cost of repair is removed from the purchase price. 

Conversely, some markets have almost no condos, so the premiums are better, but the pool of tenants/buyers is smaller because they are less accepted.Anyway, I agree.

I actively flip, build new homes and I am working on our first condo conversion in Washington, DC.

Once there it is a familiar place with little fear of going there again.Engage in conversation when they mention anything about their old house.

As long as you are not soliciting/ promoting a company as an employee or you have some association where you benefit there is no worries with making it a public conversation.