Quick write up, I am beat:

1) Passed most boats on the way to the Neuse from Cedar Island except the Isotope (he is quick upwind)
2) Slowed down in the Neuse, wind went light and current wasn't favorable. Breeze built later and we really picked up speed (double wired upwind) but angles were pretty terrible.
3) Saw JP take the mast down on his Isotope and start rowing. We pulled over and dropped the mainsail, expecting not to get through the tree. Then we started paddling (kayak paddles), which was brutal. Tried reefing the main to help get upwind, ripped the reef point. Dropped the main, started paddling again, ended up using the paddles as poles and pulling along the muddy bottom. Took nearly 1.5 hours to get to the bridge.

3) We could have dropped the mast and POSSIBLY gotten under the bridge and around the trees. Stopped before the bridge and repaired the main sail (had someone bring repair equipment). Floated over to the tree with a gentleman who had a chainsaw, helped him cut the tree, got stuck in the tree due to the current, had a Hobie Adventure Islander pull us out of the tree, and decided it was better to try and go the long way around. Chainsaw man cut us a longer pole to use getting out of the canal, so we Tom Sawyer'd our way out of the canal and got out before dark.

4) Sailed slowly down the creek out where the canal is located, pitch black, hard to see what was going on and the wind was super light. We cut the shore too early on the way out of the creek (there is a marsh, then some water, then another island right outside the creek). Hit bottom near the island, with the spin up, wind was building due to a line of thunderstorms. Managed to drop the spinnaker, get the boards up, turn the boat around, drop the mainsail, pull the boat on the beach, grab a bunch of gear and hunker down under the tarp on the island. After the rain passed, we got in warmer cloths and setup camp on the boat. This turned out to be miserable, we were freezing all night even myself in a drysuit with several layers of fleece on underneath, the wind was just howling through our makeshift tent.

5) Woke up at 7am freezing, evaluated the wind, which was blowing from the NW and the NNW at Cedar Island according to the marine VHF. We decided it would be fastest and safest to book it back to Cedar Island rather than go down the ICW, try and go through the bridge, and sail upwind all the way through Core Sound. We single wire reached down the Neuse and were back at Cedar Island at 11am.

Lessons learned:

1) 8' boat+10' tree is not less than 13' width of canal
2) Paddling a TheMightyHobie18 is exhausting, inefficient, and stupid
3) Dropping a mast after paddling, or before paddling, is liable to result in damage due to exhaustion and mental fatigue.
4) Sailing at night with no moon and only the GPS to guide you is no fun on a small boat (ok on a big boat with proper wind instruments)
5) Bring warmer camp clothes and a real tent if planning on Hobie camping.
6) Reefing a TheMightyHobie18 mainsail requires more reinforcing/don't do it.
7)Entering a race designed for kayaks and purpose-built boats on a beach catamaran is crazy.
8) Entering a distance race where there are few beaches,no hot babes,and no rum is stupid.