I have an 07 XLT, 285K miles. Had the electrical plug sleeve gasket leaking awhile back. I put the car on jacks as high as they went and had enough room to use a creeper easily. Changed the filter while in there. The fluid was still like new, bright red, so no concerns on wear and tear. The new electrical plug collar was extremely hard to get in so I ended up using the old plastic collar with the rubber seal off the new one. Fit so much easier and now doesn't leak. I filled it with enough fluid to slightly overfill it and let the excess drain out. I used the Harbor Freight battery powered fluid transfer pump to fill it. Worked great for low viscous fluids. Doesn't work for gear oil. When I put the pan back on, the rear bolts weren't tight enough due to the exhaust pipe crossing under that portion of the pan's bolts. So it ended up leaking slightly. I was able to use a wrench and tightening them until they stopped leaking.
I would suggest to replace the pan bolts while doing the job.
Additional question... is the dipstick supposed to be a traditional style range indicator like skinny8021 posted? Because mine has just threads that go into the oil.