Re: Selling this to management will be hard.
"We have systems that won't even support SMBv2 (issue at the vendor level, not at the OS) level and I consider that an easier nut to crack."
We had that at my workplace. Our attitude was that EITHER we carry on running SMB1 and it is only a matter of time before something like WannaCry tanks all operations for an indefinite period at unspecified cost to the business OR we switch off the shitty hardware. Put that way, the nut almost cracked itself.