EE here. If you can, take the liquid-tite back and get a refund. Forget about conduit. Use black poly water pipe - it's cheap and easy to work with. You aren't pulling in 120 or 240 volt wiring so water pipe is fine. Depending on soil conditions, you have a choice of the thin or thick wall type (different pressure ratings). Depending on presence of rocks and whether small round or sharp larger ones, you may want to bed the pipe in a layer of sand for protection. Bury it min. 24" below grade.
Regardless of whether you use liquid-tite, rigid PVC or poly pipe, make sure there are max. 4 x 90 degree bends. If using poly pipe, especially the low pressure/thin wall type, if it is wavy when placed in the ground, each little wavy bend adds up and can exceed the 4x90 total limit. Nice thing about the poly pipe is you can make large radius sweep bends. Sucking a pull-string through will work fine. I've always just used a piece of plastic garbage bag. You may find it easier to pull a lightweight string through first. Forget about a fish tape. As mentioned, get the pull string in right away.
You might consider installing a pull box about 1/2 way through the run but 250' is not a big deal if conduit/pipe is properly installed. If using water pipe, an ordinary in-ground plastic valve box is fine. You should use lubricant - liquid dishwashing soap or wire lube. You need to be careful not to exceed the max. pulling tension on the cable.
If under a driveway anywhere, pay attention to protection of the pipe/conduit so that it won't get damaged afterwards.