Interesting idea and you get an "A" for creativity in that regard, but I don't think in practice it would work for two primary reasons.
1. Most TM owners, myself included, hold our TM's near and dear to our hearts. Can't really give u a rational reason why, just the way it is. So I really don't want anybody, especially a stranger messing with my TM. Related to this is the special knowledge needed in using a TM, which complicates the situation and greatly increases exposure to a renter unintentionally breaking something, not to mention the occasional jerk who just abuses something " cause it's a rental."
2. When you look at the costs of hotels, vacation properties, rental RV's etc. your pricing is very low and would hardly cover the increased wear and tear. When you factor in the increased insurance cost, taxes due on income etc., replacing broken items which could easily cost beyond what you have suggested as a deposit; it becomes an easy question for me- no way, not even tempting.
And what if the rented TM is totaled by someone who does not have the much towing experience? Not only are you out your deductible, which could be $1000, but then you eat the depreciation of what replacing your TM cost and replacing it, not to mention the hassle of going through that process again. Moreover, even a new TM would not have the mods that many of us have done and really don't want to do again.
So, again nifty idea, but not this cowboy, would not even give it a second thought.
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