I just leased my 1st vehicle as well. Like you, I like to trade every couple years so have accepted the fact that I will probably always have a payment. I feel like I did pretty well. Had a 2010 ram bighorn that I owed 11k on still. Went to look into getting a 2020. They gave me 14,500 on a truck that had 12k trade value. Got a 2020 Laramie Sport with sticker price of over 57k. All said and done, walked out of there leasing it at 46900 after rebates. Turned my 300 payment on the 2010 for a 499.00 lease on a well equipped 2020. Term is 42 months and 33k buyout option after lease is up. Think I did okay?? Question is, if I get bored with it and want to upgrade in 2 years, is that going to cost me an arm and leg to bail early? Another question. I want to taint windows, rhino line the bed, and buy some more aggressive tires for winters in SD. what does that do to the lease?I purchased my last 7-8 vehicles (yes, I trade out a lot). On my previous charger, I decided to lease it. Ya, I was upside down some due to me purchasing and trading out so frequently. But, I decided to bite the bullet and just pay the negative equity I had to get me right side up and into a lease. I now lease my '19 big horn. I traded in my charger lease early, so that had some play in my final outcome but I'm at $500 a month, 3 year, 10k miles/year. I put $1,000 down which like others have said, the less down the better. I feel like I did well considering my personal circumstances. Definitely had I been at the end of my current lease, I would of gotten a better deal I'm sure. But, I'm happy and love the truck. I'll only lease from here out until maybe I'm ready to retire and actually just keep a vehicle. But for now, I enjoy trading out every year or two.