W-9 Form and My Lawn Maintenance Guy

[Nick Brubaker]

Hello all,

I have a bit of a sticky situation with the guy that does the yardwork (mowing mainly) on my house. 

He does a good job.  He's reasonably priced.  He is flexible as far as scheduling and receiving payment.  He is friendly and trustworthy.  

I still owe him for the last two times he has done work.  

I have recently past (if you count the payments owed) the $600 threshold for this year to where I am expected to get him to complete a W-9 form and later submit a 1099.  I read in the Nolo book on taxes for landlords that if I don't take care of the W-9 paperwork I would be responsible for the taxes owed by him or something like that.  

I have mentioned to him twice that I need him to complete a W-9 and have sent the form to him through DocuSign, but he hasn't responded (he has responded otherwise).  

I want to pay him for his work and want him to continue taking care of the lawn, but at the same time hesitate to send the checks before he completes the W-9.  

What do you suspect his reasons are for wanting to avoid doing the tax paperwork?  I do realize that having to pay taxes on the $600 may actually amount to the amount or more of what he is paid for a single time of mowing the lawn, but I'm happy to continue offering him business going forward.   

Am I being too much of a stickler to require a W-9 form from a lawn service guy?  Do I need to find someone else (I really don't want to)?