It sounds like you are missing a conversation with the tenant to understand the situation.

Unless the 600k property is in some crazy appreciation area, or conversely the 300k properties in depreciating areas, 1.2 million of property is going to be worth more than 600k worth of property in the future. 

Increase time spent conversing with each lead that you get to learn more about how they view the property and implement reasonable changes accordingly.

Also there is a special tax abatement for office conversions but requires the developer to retain 15% as commercial use.So we have the option to stack them and consolidate.

After a few candid conversations, they realized they could negotiate slightly higher rents by offering small improvments..things like better loading dock access or upgrading the security features..turning a so-so cash flow into something much healthier.When you break down your family friend’s situation, it might help to consider these angles:Selling and redeploying capitla could open up opportunities in markets where cash flow is a bit juicier.

We have had this exact conversation with several different trades, never a GC. 

Also, I assume a 10% property management fee in my calculations and based on initial conversations.

Then you can see how they are getting their income on a conversation.

Learned how to manage conversations and creative financing.

Always open to conversations with like-minded folks, but nothing I have specifically sought out intentionally... yet!