Since on the subject, from what I was told when I called SeaTow and BoatUS, if it is further than around 25 miles or so, and depending on sea conditions, they will not tow you in, they will call the CG to come get you. (Unless things have changed in the last couple years)
As everyone has stated in other post, sooner or later you will get caught in some mess out there.
I have always considered myself reserved when it comes to weather windows, carry 2 to 4 of everything when I go out, and look for calm days preceding and following our trips.
Even as cautious as we are, we have had some close calls, where it was blue sky, typical summer forecast "slight chance of scattered showers", smooth seas prior and future forecasted
For example, few years back, it went from blue sky slick conditions to beyond ugly in minutes.
When we broke the jetties I bet the wind was gusting a solid 35-40mph, so much so that I had to use my tabs to keep the boat running level and not healing over from the wind
As you can see in the pictures, from slick day to all #### breaking loose by the time we barely made the jetties
Had we fished 5 min longer, didn't see it on radar, buddy boat or not, I would not have wanted to be caught out there in any size rig
That's not saying you can't make runs in just about any size boat on a slick day, I'm just saying it seems like if you go enough times, it's not a matter of 'if' but a matter of 'when', and when it happens I want as much boat under me that I can afford and not rely on someone else, they may very well be fighting troubles of their own at the time