For an individually owned SFR (no s-corp), do I need to issue a 1099 to contractors for services over $600?

Having a tree removed on one and its definitely costing over $600.

Well after this I won't have any big oak trees to deal with, but I get what you're saying.

Do you see any issue with tax deductions with not filing the 1099? I'm going to have a decent net loss this year and would prefer to avoid an audit.

We 1099 every individual over $600. Our CPA is a stickler on it. We've never had anyone upset about it. We are upfront and tell them them they have to fill out a W-9 & will be 1099'd. If it's close to $600 & they're worried about it, they can reduce their price a little - some have. On the other hand, if your tree guys balks, chances are really good they working under the radar & don't carry insurance either.