I think you would feel more comfortable and confident if you had more information and resources. This kind of venture can be very rewarding and serve to add to your ability and confidence if you approach it will caution, care and diligence.
You have taken the best first step, in asking for the opinions of other sailors. I have owned many boats over the years from very small ones to quite large ones, both power and sail. There is always a learning curve with each new boat. I have found that there is not better way to learn how to handle a new boat than to spend a great deal of time in controlled conditions just going through the basics. Take it easy on your trip in the beginning and you will do this.
Then, I would do as much research relevant to the trip as I could. Get as many books on small boats, trailer sailing, cruising in small boats and about local sailing as you can and read them.
At the same time, think safety. When Navy warships go out on missions, safety is the #1 consideration on the cruise. It is first and foremost, always, even for the most well trained and seasoned crews. The same should be your mantra. Get the most safety equipment recommended for your trip and... back ups for back ups. I don''t think you need a 406 EPIRB, but... perhaps two VHF radios (monuted and hand held) and a cell phone. Back up battery for the boat. etc. Certainly LOTS of weather info and a weather radio. No doubt there are a lot of people who could give you a lot of advice in this regard. Of course get the most complete USCG safety and signalling kit you can.
I am not suggesting that any amount of equipment or communication gear can replace experience. But I think that having the most options available for safety and communication puts one in the best position should they be in an adverse situation. Many people end their trips or have to be assisted because: their boat batteries ran out, they had no flares, they had no cell phone, the cell phone batteries ran out, they had no water and it was dangerously hot, they had no charts... etc.
best of luck,