Keep your TJ and pickup truck. Buy the crew side by side and a trailer. You get to keep the TJ you love. You keep the paid off pickup, which fits 5, and has many other multi purpose uses that you don't get with a TJ, JKU / JLU. You'll be packed tight with 5 plus all their gear in a JKU / JLU. The pickup hauls your new crew of 5, with plenty of room for loads of gear and stuff, along with your trailered side by side to enjoy exploring forest roads. Also no real worries about trail breakdowns and not having a ride back. And should your relationship not work out, well, you still have your present vehicles , plus a bonus side by side.