The selling bank can care or less if your offer is vested in your personal name or an entity.The following advise is from a liability and asset protection standpoint.You should be flipping in an entity and with adequate insurance always, not in your personal name.

Since it has little to do with my short-term plans for the property and the markets will always shift before the equity becomes useful to either finance another property or something else of that nature..

Don’t rely on someone who is “decent” or “adequate” or “good enough.”

If the price of the property is adequately reduced because of these problems, it should be fine.

This would be my first project of this nature.

That's a natural thing that happens to anyone who strives to do something out of the family tradition.

My background was finance and accounting so naturally I'm concerned with ROI.

Should I push back on expenses of this nature?

I thought this was worth posting as well:Milton Friedman.....Greed Is GODDPeople are, by nature, rational self-maximizers.

Your purchase and sale contract should have covered outstanding rents etc.My buyers of commercial properties there is a standard contract however we usually employ the services of a real estate attorney to draw specific language to address concerns with a specific property.The commercial forms are generic in nature and commercial properties are very specific.Did the seller not inform you of the tenant being behind on payments??