Since you said you don’t really need the cashflow because you are sitting on huge reserves do the math based on income instead of cashflow.

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We consulted with a designer once, but saw it as no value based on what we had already done ourselves.

Quote from @Christian Styles: Hey Sam, I've used both Propwire and Propstream, they seem quite similar but propwire has a free base version and propstream does not.

Or, you could ask for a rate quote based on a range of credit scores and you can figure out what they'd charge you on your own.

Don't change jobs or income yet.Once you do and you think you can manage the payments based on your new income, maybe once you get the rooms rented.Then if you want to switch there are plenty of opportunities. 

Based on my calculations, even with a low down payment, I can achieve positive cash flow (with aggressive enough house hacking).

I charge a scaled pet fee based on the size of the dog with a premium for high risk dogs.

So it would be best for him to first understand how this would impact his taxes and estate planning then structure the sale based on that.

They didn't pay for it, so they don't take care of it like an owner.Before you make assumptions about costs based on a seller's contribution to improvements, find out what they improved?