Sea Wolf, you pretty much described the plan that I have. Explore, Drool a little, and see if the fascination goes away. Along with clear level head thinking, but it's me we are talking about!
As for the lift, I am getting a drive on dock to place parallel to my existing dock. Down here in Hurricane country any elevated structure is waiting to get eaten. So I am thinking I can replace the float on dock 2 or 3 time for the price of a lift (insurance will not cover either structure). In fact if I had one during Katrina, the lift would have been toast. Even though the house did not get any damage from rising water. As Maxwell Smart use to say "Missed it by that Much" (3 inches to be exact). The elevation of my floor is 19' 6" above sea level. The roof of a covered lift would be 16', and the electrical and mechanicals of the lift would have been trashed by salt water.
Matt, I agree, two slightly older 25's or 30's (2 stroke) come in around 115-120 lbs each. Personally I always believed if you can't decide what to do, then DO NOTHING (as long as life, limb, or finances aren't involved). So I will continue to explore, examine, evaluate, and drool over twins all the time really doing nothing until repowering is required. At least I will not be making a hasty discission when that time does come.
Brian, I am all over the stern weight factors. Currently adjusting, relocating, and modifying to meet my satisfaction with the Honda BF 50 I have now. The stern weight is the primary issue to me and the main factor in exploring the possibilities. Never was one for a kicker and it really isn't a common sight at all here in the MS Gulf Coast. Think I would adapt a bow mounted trolling motor before a kicker.