Retire from this desk jockey gig? Idk, maybe tomm, maybe in 30 years. Whenever I decide I've had enough or they've had enough, I guess. Then I'll go travel the country and guide hunts/fishes and train mutts. Health Insurance is the biggest deciding factor for many, Obamacare here we come!!!

as soon as I win the lottery, so that needs to happen.. Sooner the better

I had to google YOLO

Nah, property management companies are available in every good vacation rental market. If you pay for it cash then you really don't have to worry about them taking there cut. I want to spend more time in TN (June, July, August). The area I am looking at is great because it has motorcycle/car enthusiast interest spring/summer/fall and during the winter they have plenty of places to ski.

going to work till i die

I loved the last job I had and planned on working till I had to retire...Well 3 or 4 years ago I left work with what I thought was a kidney stone and wound up with a full blown disc and back operation the doc. ,,, I'll use that as a reference,,, said I'd return to work in 6 weeks....Well it didn't work out that way and I guess this is the hand the GOOD LORD dealt me with my piece of shoulder I got left so at 54 I was retired....As luck would have it everything I owned , house ,truck,wifes auto , boat all payed off so I can do ok....My advice to the young for what its worth,,,401K is playing the stock market....If company matches your payment put it in conservetive stock...even though the stock doesn't pay much you get 100% by company match and don't lose...Also start an annuity...I was lucky I got in one that garantee's 3.5% and will rise to 7.5%....There is also prepaid life insurance which they do not like because its a 1 time commission. The most important thing to remember is to save for when the GOOD LORD feels its time to cut you down....

Nice to know you have something to look forward to. I say do that if you absolutely have to. Or as some others have said, unless your really love what you do.
BTW, probably the best topic I've seen on here in a long time.

This is kind of what I'm figuring. I'm pretty sure this desk job will kill me before I'm 40. If I happen to make it past that, I hope to retire by 60. Unfortunately when my kids were born, they both racked up some pretty hefty medical bills. I'm still young and have a good bit of time left, but I feel im a little behind the 8 ball on my goal.

Don't know, I really haven't given it any thought. I guess when I get tired of working.