However, these strategies require careful financial analysis and planning to ensure that you can obtain sufficient cash flow to cover your expenses and debts Isn't it 7.5?

NON-SUFFICIENT FUNDS .

If so having it as the named insured is sufficient, and don't need additional insured with your name on it.

I would like to update the propriety but lack sufficient funds and do not want to tap into my savings.

It's a two-family so the basement for sure does not have the proper egress for sleeping quarters, much less a separate unit.

Noise too because you will have night shift people that want to sleep.

I agree a spreadsheet would be sufficient for me with only two units. 

Also to make it legal, you need to make sure you have sufficient egress, fire separation between upstairs and downstairs and technically you need entirely separate mechanical/plumbing/electrical systems.

Continue doing those things that make you happy, and let you get a good sleep. 

So when I loose a deal I don't loose any sleep over it because I feel content I would have over paid if I got it.