Yes, Maui is very anti-smoking. No lounges at all.
But, big but, the hotels and golf courses are very accommodating towards cigar smokers.
They'll kindly direct you to a nice smoking venue where you can plop down and herf... The Four Seasons receptionist walked us out about 100 yards, pointed to the shore and said anywhere you like.
Jen and I would opt for a scenic golf hole (way off the tee box of course) and enjoy ourselves with a smoke and beverage.
Simply put, anyplace away from people and have at it. I always had my morning and evening smokes right on the water in front of our condo. Never a complaint.
Kahului will put you smack dab in the middle of the city; where you'll land.
You'll get more of an island feel if your stay is on the outskirts.
Wailea is very quiet and dry. Once you drive past the Kealia Coastal Boardwalk the flora a fauna diminish until you head towards Haleakalā.
All the beaches are sandy and relaxing. Not much of a night life on this side of the peanut.
Lahaina is the greener wet side and has a great night life. All the eating/bar establishments on Front St. are oriented to view the scenic ocean and people watch.
Maui is small enough where finding a stay centrally located is unnecessary.