One of the topics that comes up from time to time with a couple of riding buds, normally after a few beverages, is that we should go in together and purchase some property somewhere in the Northwoods of Wisconsin or in the UP (where we ride 90% of the time). Since we're all fairly young and work way too much and have family obligations and therefore can't get up North as much as we want, the idea is that this would work out great if it was possible to rent it out quite a bit to help offset the costs. Obviously property rentals are full of risks and partnerships can create issues, but putting that all aside, does anyone have any success in renting out property in the UP or Northern Wisconsin? Ideally, we would like to rent it for nearly all of the summer/warmer months and probably more than half the winter weeks, just using it ourselves for the three or four times we get up there each year. Probably have to get a rental management company involved I'm assuming. Stated another way, it would essentially be a rental property where we could store our sleds that would slowly build up some equity. Seems to me that this would be difficult to pull off without it turning into a money pit, but I'm curious if anyone else has had some success with this.