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Paying expenses for rental property without 1099?

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rated:
I have a rental property in AZ and a management company that pays various vendors to do stuff. It just became a rental as I used to live there.

For them to pay my longtime landscaper, they want to have a 1099 and get his name/TIN/SSN or whatever so they can record for tax purposes.

He seems apprehensive about it which is making me think he might be illegal. So all politics/opinions aside, is there anyway to continue using him as some sort of misc expense?

To address the illegal's part of it...there's almost no avoiding using them. Either 1 US citizen will setup an LLC and get a TIN then hire a bunch of illegals and pay them under the table or this guy and his wife are independent, so they don't have the benefit of having some shell company.

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rated:
You give them your SSN...which is very illegal.

Business that want to stay on the 'right' side of the law needs to get an W9 for all vendors. (He gets the 1099, he doesn't give them a 1099). Especially when they get audited.

rated:
Your management company is doing it legally. Good for them.

You could come up with some way to do it illegally but your management company might not go along with that.

rated:
forbin4040 said:   You give them your SSN...which is very illegal.

Business that want to stay on the 'right' side of the law needs to get an W9 for all vendors. (He gets the 1099, he doesn't give them a 1099). Especially when they get audited.

  
I would not do that. It's like $80/mo or something, which I was thinking could qualify as just a miscellaneous expense because of the low amount, instead of setting him up as a vendor.

rated:
The threshold for 1099-MISC to individuals is $600/yr.

rated:
You can remove "landscaping" from the management company's list of responsibilities, and just handle it yourself.  There's no way to make "looking the other way" legit, but if you are going to do it anyways it's best to have as few hands involved as possible. 

Or, since you are paying a management company anyways, you can let them do their job and hire a legit landscaper.

 

rated:
If I pay him directly, then I'm not sure how I'd deduct it as a rental expense unless I just list it on my taxes?

There aren't really any legit landscapers...only ones pretending to be legit. I hired a "legit" company, Moon Valley (big company), and had to contact them 15-30 times to get them to repair their previous work.

Sounds like I might be SOL.

rated:
jerosen said:   The threshold for 1099-MISC to individuals is $600/yr.
  You can issue a 1099 for $1.  You must issue a 1099 if the amount is $600 or more.

rated:
Al3xK said:   If I pay him directly, then I'm not sure how I'd deduct it as a rental expense unless I just list it on my taxes?

 

  Is your property management company also your CPA preparing your tax return?  How else do you deduct anything, but to "list it on your taxes"?

The issue is paying him more than $600, which requires you give him a 1099; deducting the expense is still legit regardless.

rated:
Glitch99 said:   
Al3xK said:   If I pay him directly, then I'm not sure how I'd deduct it as a rental expense unless I just list it on my taxes?

 

  Is your property management company also your CPA preparing your tax return?  How else do you deduct anything, but to "list it on your taxes"?

The issue is paying him more than $600, which requires you give him a 1099; deducting the expense is still legit regardless.

  
I normally paid by cash, so my accountant would want receipts, but I could switch to check.

Good news though, I had a Spanish speaking friend call him and he does have an ITIN so we can do a 1099. I guess language barrier was the problem.

rated:
I would inform the management company they should use a Spanish speaker when they call him.  You can also instruct them to use this particular service for your property.

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