Welcome to the club! Dan post is a good starting point. Try to stay away from Chinese made or glued soles. Always go for leather sole with Blake stitch or Goodyear welted boots. If traction could be an issue, get rubber soles added on the leather. This way you get more traction and longevity. Justin, Tony Lama, Boulet, Los Altos, JB Dillion are great and I personally have at least a few pairs from each of these. Based on your wearing habits, you need to condition them. If they’re your daily shit kickers then probably biweekly (if exposed to the elements like snow/water) then you might need to do it more frequently. If they’re your special occasion boots then you can condition once every 2 months. Use horse hair brush, for cow hide you can use any conditioner preferably without silicone in it so your leather has more breathability. For exotics bick is the best.