Basically your trying to shift the land bank fee to the seller. Good luck with that. Everyone tries that. Or tries to split the fee with the seller... I will tell you that you will get some resistance from sellers on this issue. However, given the soft market today, anything is possible I suppose. Timing is everything.
I still think renting is better for the visitor. You need to look hard at the numbers as well as the other people issues. Look at what your yearly nut will be and ask yourself, what could I do with that money? Also you need to consider the large headache factor this will cause for you managing 40 guys all wanting to come the same time, not to mention maintence. This is like selling ski timeshares...no one wants the summer months, they just want a few weeks in the winter.
The RE trends are changing.....I know a few very wealthy people who have all sold their summer mansions in the 5-8 mil catagory the last several years. I go fishing with this one guy fairly often and asked him why he sold that awesome house. He said, " Look, I can make 500K+ per year in interest alone on that money, I can rent an even better house for 100K per summer and walk away without the headaches of having to worry about it all winter with 400K in my pocket. Heck it cost me 50K just to paint that house. The days of 30-100% gains/year in RE are over out here. Its a no brainer. " Your case is the same deal only one less zero on the end.
IMO for the visitor who will be here in short stints, renting is the way to go . Renting year round even. The big run-up in value like in years past is over, or at least it is more tempered now, could even decline some. You might consider that too.
It might turn 40 friends into 40 enemys. Most deals like this have issues.
Why not just give the money to JohnR, and let him move out here year round. I am sure he would build a nice sb fishing shack out back to house you guys like a mob of Brazilian workers for the few weeks your going to be here
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