Transporting mid size 4 stroke

2015 50hp tiller 4 stroke tohatsu long shaft...230ish lbs
Option #1....Thinking of building a trailer hitch style mount, to transport it upright approx. 5 hour drive
Option#2...Tow the boat 5 hours there, 5 hours back, use buddies cherry picker to install
Options #3... Take cap off my truck, drain the oil, fuel vapor whatever iser, lay and strap on pallet, find chain fall and tree to install outboard.
Almost want to do option #1, but alittle concerned with the strength and the longish haul. Thinking a reese hitch can hold over 1000lbs toungue weight so a 230 lbs motor would be fine?
Thoughts?

I towed my last one 150 miles. I used a small 4x6 foot trailer with a motor stand in it. Used some straps to tie it down in place and didn't have any problems with it.

drain the oil from the motor. Lay it on a couple of blankets in the back of your pickup.

I like your chain fall on a tree limb idea. I did exactly that when I stripped my boat down to the hull to paint it.

I also built something that looked like a tall sawhorse with wheels on one set of legs. I mounted the outboard on the sawhorse and added long handles so I could roll the motor around sort of like a wheel barrow.