Lenders on commercial deals typically want to see a debt service coverage ratio (DSCR) of net income = 1.25x debt service, at the very least.  

As long as they are on the same deed, you should be able to get one policy with some tweaks in coverage. 

lol Has anyone out there found a company that will write a policy for this kind of coverage??

. - 100% Commission, $300 transaction fee, $19 per month, Board of Realtors Membership is optional, Free FMLS access / GAMLS is optional, E&O Insurance - $1mil Coverage, No Annual FeesCan someone point me in the right direction?

We require all of our tenants to purchase renter’s insurance and name us as additional insured on the policy (that way we get notified if they let the coverage lapse).

If you're trying to save money you could just decline owners coverage on the first transaction. 

Axel Meierhoefer,  I have invested in several sites, and also did a comprehensive review of the top 100, including interviewing other investors using those sites.  

A good Realtor provides a comprehensive analysis, advice on making the home market ready, guidance through the offer and negotiation process, a ton of referrals for various industry professionals in the event they are needed, a marketing network that is far beyond "it's on the MLS" (i.e syndication and social media), and the backing of a brokerage that ensures every part of the transaction is handled not only within the law, but in a way that protects you.

I forgot to mention that I had a state certified land survey done as well to show exact property boundaries, so that increased my title insurance coverage.

That said, yes, the reviews aren't particularly impressive, so I guess it's still a topic that could use better coverage.