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

If you're looking for some direction and want to have a conversation I can commit to honesty and transparency, not pushiness or gimmicks.

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

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.

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

Maybe the answer isn't "replace your W2 as quick as you can" but maybe the conversation needs to be how can i lower me expenses, while still enjoying life, and maybe just doing a job that pays 200k with no expenses and a few rental properties that bring in some income.

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

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