I probably do less than 5% of my walking in boots so, even if money is no object, I wouldn't want to spend it on a pair of boots.
I prefer to wear whatever best suits the weather, the terrain, the time of year and the type of walk I'm doing (speed, distance, ascent). I certainly don't believe there is a 'best' boot or shoe that works well in all situations.
So with money being no object, my recommendation would be to buy several different pairs of footwear to cover all possible requirements. An additional benefit of this approach is that it encourages the practice of footwear rotation - that is, wearing different boots/shoes can help prevent damage to feet (blisters, etc.) and it can involve using different muscles while walking.
I practise what I preach... in addition to my pair of Scarpa R-Evo GTX boots, I have 6 pairs of walking/trail shoes on the go at the moment. Two pairs are waterproof (Scarpa Vortex GTX and Salomon Sanford GTX), while four pairs are non-waterproof (Merrell Cham 7, HigherState Soil Shaker, Garmont 9.81 Grid, and Asics Gel Trabuco 9). It's not just the waterproofing that matters, each pair has its own degree of grip, weight, support and comfort. Best of all worlds!