The biggest problem you will run into is if you hire an illegal immigrant, or if the company you hire uses an illegal immigrant. I wrote several posts about my company having 18 worker comp claims and 3 civil lawsuits filed against my company between 2015 and 2018. The worker comp claims were not a problem, but the 3 civil lawsuits meant I had to hire and pay an attorney and the cost for my attorney and the ''Go Away Money' cost me $180,000 from my pocket and I got away super cheap because the attorney I hired is a woman and she works hard to keep costs low, but my attorney fees were still $75,000 for just 1 case and I paid the Plaintiff and his attorney $65,000.
There is a new fad where in 2015 attorneys figured out how to capitalize on several new laws that went into effect in 2000. So, starting in 2015, employees started filing CIVIL LAWSUITS for not getting 10-minue uninterrupted breaks every 4 hours (actually every 2 hours, but I don't know why the laws says 4 hours), for not getting a 1-hour uninterrupted lunch break, for being mis-classified as an Exempt employee (independent contractor) when you report to the IRS, for not getting proper Wage Earning Statements, for not getting paid overtime, for age and race discrimination and the list goes on.
Here is the worst part. No attorney cares whether or not you are innocent or guilty of any of the above. They file the lawsuit, anyway, because they know you will pay money to settle through mediation to avoid your having to pay your own attorney up to $400,000 to prepare to go to a jury trial and then they know that even if the Plaintiff wins only $1.00 you will have to pat the Plaintiff's attorney and that could be another $400k.
If you don't think this can happen to you, then you are 100% wrong because when a lawn mower's employee is injured even when working for another customer and that employee sues his boss then you had better be prepared with EPLI insurance because YOU WILL BE NAMED IN THE LAWSUIT and that means you will be sued and you will need to retain an attorney. The average attorney you call will want no less than $5,000 to $15,000 for a retainer and my attorney works super cheap and some of my monthly bills was $21,000, JUST FOR ONE MONTH.
After reading your post, it sounds like your wife is getting frustrated, worrying too much and micro-managing the paying of the lawn mower companies.
We own several properties in several states and we deal with many lawn mower companies. My wife gets the monthly bills and we never required proof as to whether or not the company cut the grass nor did we ever care how many times the company cut the grass AS LONG AS WE NEVER RECEIVED COMPLAINTS and we never received a complaint about the grass not being cut nor did we ever receive a complaint about the grass being too high,
Just pay the bills and if you get complaints then deal with the issues.
Check on EPLI insurance because it is not expensive and will protect you in case someone files a civil lawsuit. One new group of people filing civil lawsuits is onsite apartment managers. Many apartment managers are claiming they don't get paid for overtime, don't get Wage Earning Statements and they claim they are employees and not independent contractors meaning they sue you for filing them as Exempt from paying taxes when you should be withholding taxes from their earning, matching their payroll taxes and paying into social security, medicare, etc.. You may not think it will happen to you, but all a manager needs to do is to either get greedy and want some easy cash, or should you anger your manager in any way and some friend gives them the phone number to an attorney then you you had better be prepared to pay no less than $100k to make the case go away, or maybe up to $250k.
I had a mediation to settle a case the day before Thanksgiving. The mediation was $10,000 for just 1 day. My attorney attended the Zoom meeting with her Junior Attorney. The cost for the mediation for 1 day with my attorneys' fees was $23,000. My ex-employee was suing me for $1.2 million. Since I was paying $23,000 for 1 day to have mediation through Zoom I was highly motivated to settle that day. My ex-employee's attorney was threatehing to take the case to a Jury trial. So, the mediator asked me for my highest offer and the Plaintiff's attorney does not hear any conversations I have with the mediator. So, the mediator spoke with the Plaintiff and the mediation said they would accept $65,000.
Everyone knows I did not owe the Plaintiff one penny, but everyone also knows that I have to pay something to make the case go away. Of the $65,000 paid, I am betting that after the attorney took all his cut the Plaintiff probably waked away with about $8,000 and my total cost with my attorney for that case was about $135,000.