You won't go wrong with either.
1. Yes it is more comfortable than my previous 1200 Goldwing and the leg forward is what I needed for relaxed feel. You may need to look at different handle bars to bring the pull back toward you. The RSTD bars work great.
2. Being a Nebraska native, I have found that the wind blows everywhere and can be strong everywhere also. The Venture handles wind like a hot knife through butter.
3. Ventures are good to 200,000 + miles, I know of one at 300,000 + miles in Atlanta.
Follow your instincts but again, either will fill the bill.