Option 2 sounds ideal.
The cruiser is for snotty days and taking big groups. Get a fast V for smaller groups and just having fun.
I'd get a minimum of a 37/38 to handle LOTO, my preference is a Top Gun mostly for looks and name recognition, not an expert in the bigger boats.
You could of course get a 150K cat that is as big as you can afford. This would get you the cat experience now for the insurance when you want to go all out on huge power 40 Skater. Something like http://www.offshoreonly.com/classifi...o37630-en.html
(I didn't search much, just grabbed the first nice cat in that price range as an idea)
Either way, nice "problem" to have making this decision.