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The limiting factor that seems to hold me (and most every hunting buddy I have) back, is time.
I have probably at least ten hunts I want to do each year, and that's with only building points in 3 different states. I have the money, points and gear to do these hunts, but what I'm limited by is those 28 days of PTO I get each year. Luckily I live where I hunt a good portion of the time, so if I'm not working between September-December, I'm able to hunt. It still is incredibly frustrating how I'm limited time-wise.
If I were to start over, I would try to choose a career that would give me more time to hunt in the fall.
I'm constantly reminded of Jim Harrison's quote, that Ben Long uses in his signature- “The danger of civilization, of course, is that you will piss away your life on nonsense.” That seems incredibly fitting.
Lots of great info there.
As far as finding a partner, of course everyone is different, but I'd rather have no partner than a mediocre one. Traits I'd look for in a partner:
-Good attitude
-Wilderness savvy
-Learns stuff quick
-Physically fit
I'd rather hunt with a pleasant person who will work hard (whether or not they've ever held a gun) than a tool who has been hunting for forty years. The ol' internet seems abundant in the latter.
As for hunting related advice, dump your points often. Point piles are like septic tanks, if you let them build for too long you will probably regret it. I think that was my biggest mistake along the way. I should have been burning points more often. Since realizing that about seven or eight years ago, I've dumped a lot of points and enjoyed the heck out of those lower and mid-tier hunts. Now, if these states would just take my sheep points, the deepest end of my septic tank of points would be cleaned out.