Thanks for all the positive responses. I had not even considered some of the things you guys mentioned. I will continue camping, be diligent with the maintenance, and stop worrying about the "what if".
Caveman, I too had some of your anxieties. I looked for 3 years for the "right" trailer and had to drive 7 hours to get the one I wanted since this model has now been discontinued. I was so afraid they would total it having no idea the cost or effort to replace the roof and I would be back to square one looking for the right one. I was pleasantly surprised with the estimate..
A quick shout out to Progressive Ins Co. and Burton Campers in Calera, AL.
Process has been quick and painless so far. I'll update this if things change.