I would point out the extra $$$ he would make with the longer term and see if you can entice him with that. 

◦Make sure the company does not entice you with a low management fee then nickel and dime you with miscellaneous and hidden fees.16.

The cash offer is enticing and closing quickly would be great so I can move on to the next project, but it cuts my profit over 60%.

The one year upfront rent sounds enticing however it's almost too good to be true.

Additionally, what are some marketing strategies to entice people with good jobs/credit scores to sign leases? 

As a rental owner, what kind of marketing piece would entice you to look into a different PM than what you already have, or consider using a PM for the first time?

I like my til deaths to be as short as possible,  but I am old and cranky and a few hundred bucks in 'extra cashflow' doesn't entice me like it used to. 

That's what's so enticing and my major hope that some aspect of that applies here.

You need to escalate in large amounts to make your offer enticing over the 2nd place one.  

Similarly for "unused" chimneys - are they snow capped or bare (heat escaping the building);Windows - broken thermal pains are obvious;Heating Plant (boiler/furnace) - is it running correctly or are there issues (gurgling or short cycling);Tenants - are the windows and/or storms open (with the thermostat cranked) - we reduced the previous owner's heating bill by compelling  enticing the tenants to keep the windows closed during the heating season.The key is to profile the "unloved" properties when they go on the market in spring or summer and then buy them in the dead of winter.