They can work with us in having dept coverage ratio of 1.1 for our rental properties which will allow us to secure 5 mortgages (max allowed with CIBC) with them without needing a crazy amount of income which is needed with other banks were using the total dept service ratio. 

Ask for lost rent coverage.

The buildings are owned by an LLC and we're looking to buy some commercial umbrella coverage for the LLC.

You may be able to place an insurance claim if you think it is beneficial, but I would only do that if the cost was high to avoid rate or coverage impact.

If another 2008 is coming I’d rather have as many cash flowing rentals as possible so that I have supplemental income.

There's also the option of a debt-service coverage loan.

You want them to have Workers Comp coverage and a GC licenseMeet them on-site when they go for an estimate so you can meet them in person and share your vision for your renovation or have your realtor or PM meet them in your stead. 

If I have this supplemental income I won't have to work anymore, barring no unforeseen rent decreases due to economic crashes. 

If your carrier is not okay with you renting it out on a short term basis you will need to find coverage elsewhere. 

There is media coverage of this story and could result in good PR for party or group that is able to help relocate these residents.