The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Cover half the mortgage/utilities/insurance/taxes etc 4.

As mentioned if the holding company is not solely holding or owning assets together funneling monies as a loan would further complicate if there is a default but also cause you to file extra tax returns = $...Yes you are taxed on interest income or any money that you make, does not matter how you structure it, what comes into play is not how much your taxed but how much you pay someone to figure out for you how much you need to pay and each layer is an added cost. 

0 Chance.Cmon, pay for insurance or just don't own real estate.Trying to gain an extra 2-3% ROI and risk your entire principal is just stupid.Don't be cheap, get insurance.

If they wanted to send a hard money pre-approval for half of the purchase, then either A) the lender needs to confirm that they verified the borrower possesses the remaining cash to close, or B) the borrower needs to show proof of funds for the remainder.

It's easy to obtain, costs very little, and doesn't require extra, on-going effort to maintain.

Consider the extra expense a capital contribution to the equity provided these are in good locations. 

If they can't/won't pay the increase, reward them with an extra 30 days to move.

I just finished a total gut and rebuild of a duplex after a fire, and listed my 2 units a week and a half ago.

Much will depend on the price of the property, for sub $100k I’d expect to pay something extra.