I recently completed the trip from Chicago to Mobile, AL. When in St Louis, I met a solo sailor who started in Minneapolis. He was making the trip with no
instruments (depth, e-charts). He had a few stories, but was making good progress. BTW: he was probably 70 years old.
I originally planned to go to
New Orleans when I started the trip. But after 3 weeks on rivers, I changed plans and headed to Mobile using the "easier" route". Good timing can be made on the Mississippi from the
current. But the distance between provisions and
fuel can be a problem. A deep
draft can be a problem getting into the popular and protected
anchorages. Debries is always flowing down the river, which ends up on the
anchor rode. Also, the Mississippi can be very high or very low. The
depth can change by more that a foot each day.
On the other hand, Fatty Goodlander takes this
route without any trouble. Also, I have another acquaintence who has made the trip down the Mississippi twice in a sailboat (now on a 47' metal boat, not sure of draft). He will tell you that the trip isn't as hard as some claim.
In my opinion, this is a nice trip to have behind you. I wouldn't find any satisfaction in being a "Looper". But other love it.