Do these messages disclose that you aren't speaking with the actual owner if you aren't? 

For a long term investor:Would it make sense if you could buy the home at a steep discount and then let the owner stay rent free for a specific period of time?

Short term rental permits are only granted to owners who will be renting their primary residence.

The answer is yes, but it is generally found when the owner is also living in at least one unit (aka "House Hacking").

Owners have been turning theirs into LTRs.  

The owners refused my advice to reduce price and they both sat vacant for months.

I'm an Asheville STR owner and a broker on the Cashiers/Highlands Plateau.

You can add different ways to reach out to improve your conversion for owners you are hitting or you can increase the amount you are sending. 

Account Closed a PMC has two options to get liability insurance (tenant slip & fall) protection:1) Get added to owner's policy as Additionally Insured (NOT named insured).2) Setup a master commercial policy and add every property they manage to it and then charge those owners the cost of the policy.Otherwise, a PMC CANNOT get liability coverage on a property they have no ownership interest in.So, nothing wrong with their request.

I’ve had most luck with signs in front of my plaza and word of mouth - networking at Chamber of Commerce and chatting with other business owners in the area.