We pay quarterly, but got good references beforehand and he also does work for many in our neighborhood. So far in the last 6 months he's been just great. Guess getting references would be best. I would think monthly should be just fine if people in your neighborhood recommend and he's been doing this kind of work for awhile. Good luck!

pay up
 

If your neighbors are happy paying a month ahead shouldn't be a deal breaker

If you have cable, I believe you pay that "service" in advance.

This is not a 15,000 contract. It is lawn mowing. I do not receive a bill. For four years I have paid the same person in advance 100 every two months. He does a wonderful job and is very reliable. If your neighbors recommended him then trust your neighbors.

I am in the habit of paying the lawn service (a one man operation) at least three months in advance..my wife and I are going away for three months so we pId him 'six' months in advance. I also give him a Christmas bonus and a Thanksgiving turkey.

Just a thought, if he doesn't trust you for a measly 75 bucks in advance why should you trust him?

I pay for the month starting, which means I pay him in advance. Figured if he took me for my money, I would not longer use him, and I’d back-talk him. He has never let me down.

He also told me to pay to his PO Box, but we make a point of seeing him the last week of the month to pay him for his following month. If I have extra work to be done, I ask him to do it. He usually does it by the following week, if he’s pressed for time. I pay him for that, too, on the day I request the work, once we’ve settled on a price. Not because he asks me to, by the way, but I figure I would continue the pay-in-advance process he requested at the beginning.

I started using him because, like you, my neighbors were using him. I prefer doing business with the little guys, rather than big companies, cause actually I’ve had more problems with the big companies than the smaller enterprises. I would trust the word of mouth of your neighbors regarding the person’s integrity and professionalism. And, by the way, I figure the reason the person asks for money in advance, because he has been taken advantage of by the customers. I know for a fact that my guy has. Neighbors are here part time, “forget” to pay him when they’re heading out, get a different person when they come back. Dishonesty runs both ways and both parties are wanting to protect themselves.

It’s a reasonable request to ask for 1 month. It’s not like he’s asking you to pay for a year. I just started with a lawn service and they billed me before their first visit.

I am billed one month in advance for lawn services rendered by my lawn services contractor; no issues.

Mine was recommended by my next door neighbor when I moved here. I pay him a year in advance. Easier, in any case. I pay for swimming pool care a quarter in advance.

My lawn man bills me for service rendered. So easy now with email.
Then I just mail him my check.

Apples and oranges. A cable company is not going to be a "no show". And no, I don't have cable TV, but I do have Century Link for internet. I don't think Century Link is going to stop my service, as long as I keep paying. Can not compare the two.

That’s the way my yard person does it and he has 5 of my neighbors as customers as well. I Just put an autopay in my bank account the 1st of the month and never worry about it.

Pay my guy since 2009 every other Month. He's never missed a week period. Always have a cold beverage for him and his helps if they're with him. Only been him and 1 other person since Covid. Does 1/2 my block.

WOW $15k
 

$15,000? Was that a lifetime mowing agreement?