Wow. That is quite a saga. I thought I was obsessed with my boat...
First of all, congratulations on making the progress with Senorita that you have done.
I can't comment on what kind of sailing you might find on the Mississippi near Memphis. I sail in a smaller river (Hudson, in NY) and we had a ton of flotsam in our river from the rains of 2 tropical storms this year. I imagine that flotsam is a way of life on the Mississippi. I'm certain you will have stronger currents in the Miss. as well.
Recreational boaters often use the Tenn-Tom waterway to avoid the bottom of the Miss.
Tennessee-Tombigbee Waterway Inland Shipping Transportation
I'm not sure about your air or water draft for taking that route though.
As a first step I'd suggest considering moving Senorita down the the lower Chesapeake, perhaps the Deltaville, VA area, as it is warmer and likely cheaper then keeping her in NY.
I'll also suggest that you check out the wooden boat forum: The WoodenBoat Forum
which, as you might imagine is mostly about wooden boats and has a slightly more international membership (then sailnet).