[quote=KarlP;1020144]With both sails and an outboard I'd advocate inspecting your rudder carefully, carrying a spare tiller, and learning how to read a chart so you don't run aground. Those will dramatically lesson the likelihood you'll use that towing insurance.
That depends on where you sail, and how recently the charts were updated. Hurricane Sandy played havoc with my area. I'd rather have the insurance. It also comes in handy not only when you run aground, but also when the engine dies in heavy winds and your marina is upwind, when another boat hits you, when you're fouled on something, etc. To me, the $125 or so is worth the peace of mind, and I'm frugal.
If we're talking about a less than $5k boat with an outboard and porta potty, there aren't a whole lot of systems on the boat. A good condition used 6hp 2-stroke outboard is in character with the boat and ~$400. I skipped the survey on my Cape Dory 25. I'd been power boating for decades and brought my dad along to look at the rigging.
Not all of us have a dad who can inspect the rigging for us. That would make things easier! If you're new to sailing, it also helps to have someone who knows what chainplates are and how they tend to corrode, how to inspect a sail, or any of a number of other potentialyl expensive problem areas. In my case, with my C25, I had a swing keel. There are stories (admittedly not many of them, but confirmed none the less) of the lifting cables coroding so bad as to fail, allowing the 1500lb keel to "free fall" around the hinge point. The keel trunk wasn't designed to handle that much weight crashing into it, and it tends to cause the boat to sink fairly quickly. As with the towing assistance, I think the peace of mind that goes along with having a competent surveyor look at/for those kinds of things would have been worth the cost, and I only paid $1000 for the boat, including the outboard.
I went the used outboard route after the one that came with the boat died, and that was a mistake. Thankfully, the guy I bought it from was an amateur mechanic, and bought it back from me. After 2 engines dying, my wife decided she wasn't comfortable with anything but a new engine. That was a $2200 investment. Again, YMMV.
x2 on the trailer - It is MUCH easier to work on a boat in your own yard!
Can't take issue with that one!