throwing good app money after bad and repeat

I don't lose sleep over it. I'm lucky enough to be in a financial and relational position to where I can apply for about everything I want, and still donate to conservation groups. I did however, drop out of CA two years ago. I anticipate I'll be doing a few trips to AK for caribou and moose.
 
I don't have many things on my "bucket list" but a sheep hunt is #1 so I'll kep throwing money at every opportunity I can. I also have a fund growing to just buy a hunt down the road too. Unfortunately none of my 3 kids have any interest in hunting and my hunting buddies are losing interest so it is tough to keep the dream alive. I'll keep playing the lottery in the hopes I someday win something and if I don't, hopefully the money goes to help the game.
 
I began applying out of state in earnest in 2001. That is when I had PTO for the first time in my life. I made a matrix of states and species and defined each one as a Long term, Mid Range or short term target/goal. By 2006 I was taking 2 weeks to hunt two different non res states. In 2009 I had three archery tags for draw hunts and whiffed on every hunt. It only spurred me on...

2010 I drew a great archery elk hunt and was successful in two states. It lit a fire in me through 2016. The effect of giving away 1/2 of my assets made me reconsider where my cash was going. I identified what states and species were really important to me to keep my skin in the game. I ended up abandoning most M/S/G hunts. Since I was not Max points in anything I focused on tags with random opportunity. I quit buying point only and applied for the long shots in states without PP's

In that time Wyoming general Elk and region deer tags became harder and harder to draw. All of a sudden I didn't have a reliable out of state hunt to count on. I started buying points in anticipation of my nephew graduating college. My father and uncle aged and I re evaluated who my hunting buddies of the future would be.

I think the best course of action is to create a "Sinking Fund" for applications and hunting expenses. The Ramsey Way would be with a dedicated free savings account and a Debit Card. Spend 12 months putting in a couple hundred dollars then apply for what you have cash to pay for. Over multiple years it SHOULD build up. The Risk-Reward ratio will determine your choices pretty easily.
 

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