If you transfer title to an LLC, make damn sure you contact your insurance carrier and transfer the policy into the name of the LLC or you could be without coverage.

Your insurance carrier will notify the lender when you switch up your insurance type/coverage/etc.

That is some nice supplemental income when you are retiring, but it all depends on your personal situation and what works best for you. 

Quote the insurance with limits and coverages you are comfortable with. 

New National lenders have come into the market offering a bit of a hybrid product, Debt Service Coverage Ratio loans (DSCR) however they require much more underwriting and time than a hard money loan.  

If you put the title of the condo into an LLC you need the insurance policy to have the LLC as the named insured.If you are worried about Liability, an umbrella policy may be a less expensive alternative to give more coverage. 

I'm not 100% sure what viewpoint you're coming from with the question but here are a few possible scenarios you may be considering...1.) you're inexperienced as a party to a real estate transaction, and you want to gain knowledge while also setting yourself up to earn income and save commissions.2.) you're an experienced investor and have been a party to several deals, and you just want to save commissions, get easy access to properties, all while helping the occasional friend/fellow investor as supplemental income.I'm guessing you're closer to #1, and your intentions must be abundantly clear... do you just want to avoid commissions, or are you in it to learn and grow in the business? 

When the property manager knows there is a large group e.g. 10+ and or kids, he strongly suggests this coverage.  

As an owner-occupier, I was once given the advice that I could just get a regular policy, but in your shoes I would ask about an umbrella policy to give you additional coverage - especially with two other units and sources of liability. 

Insurance kicks in as long as you have proper coverage.