Leasing a trailer; with work

Hey guys,

I have been following this forum for a very long time and have found it helpful for basically anything truck related !

Alittle background; I am fully independent owner operator with my own truck and float trailer. Have been in business just over two years. I am looking to expand/grow and am considering a number of different options (different trailers/trucks/hiring drivers, etc).

The question I have today is, I have the option to purchase a ‘53 dry van trailer , that comes with year round steady cross-border and work. (I am Ontario and the run is to Virginia and back). I’m in the midst of getting all the details about the pay/type of load etc so I will update this week when I find out. What I’m wondering is; I have a good reliable driver that has just purchased his own tractor; and is going to be rolling this spring. I’m looking at brokering this run to him , with some sort of trailer “lease” (as I will own the trailer outright, and he would be paying me to use it for this run).

1) I gather I will have to some insurance coverage of my own on it, as well he would have his own coverage on it as well?

2) What other liabilities would be required of me?

3) Does anyone have experience in this sort of situation and if it is even worth it? Lol . Maybe it’s too much of a headache but I thought it would be a good way to make some extra money while having someone else work my trailer .

I appreciate any insight and wisdom!

Neil