Not that I ever know what I am doing (if you don't believe me ask her indoors) but when I buy anything I always buy second hand and at the low end of the market. This way I never get the feeling that the cost of what I buy makes me feel bad if I don't use it all the time. Also the chances of people nicking it or worry when you ding it is so much less. I also think that you have more fun with smaller cheaper things as you tend to care a little less about them. Also if you shop around and are prepared to travel you can actually pick up some very good items for cheap prices:
For Example our little 2 berth caravan cost £3,500 in very good condition (new cost £21,000) we have had it about 6 years and use it about 2 - 3 times a year. Keep it at home so no regular costs. I already feel we have had the full value from it for what we paid and we still have it
Another example is my 17 foot Fletcher Bowrider. Cost £5500 have had it about 4 years and use it about 10 - 15 times a year (would use more but also have other boats). With this one I recon I have also had most of the value and still have her.
The best example is my recently purchased little rib for £2400 which I have had about 3 weeks and used 6 times already.
If you add that lot up it is £11,400 for 3 toys which I feel is quite a small about of cash and I don't stress myself if I don't use some of them that much.
Also never divide costs by number of uses. That will always depress you.
Don't get carried away by shiny newness that will just cost you
When you buy always think that is that money gone, When and If you get any back that will be a bonus.
Then the most important thing of all............. always think of ways and reasons to use your toys never reasons not to use them.
As I said I generally I don't know what I am doing, am impetuous, too fat, Spend to much, Have far too many toys and am about to retire so I will have to change.......Or will I

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Regards
Dennis