For multi-generational families, designing the right second home is often a series of "both/and" propositions. A home needs to be both a reflection of self, while also foreseeing the needs of generations to come. It needs to feel cozy and intimate for weekend getaways, while also welcoming large gatherings. Most of all, it needs to understand your needs today, while also anticipating your hopes for tomorrow. If your goals are both/and, it's important to have three specific strategies in place.