I had a similar idea and actually did it only with a rental house. In November the house was 8 years old. Now the house shows 2 times the wear of others, 'worst home in the neighborhood', it needs new everything. the House has been on the market 4 months with NO offers, none, I’m listed at 20% below the appraised value.
Bottom line; ALL my 'acquired' equity is going to be spent fixing the place up, just to sell it for what I owe the bank. A ‘Cash at signing; offer is not generating offers, I am being forced to repair everything. Looking back, considering the yearly upkeep, mortgage paid when house was not rented. I’ve lost thousands of dollars, and I won't even discuss the headaches this 'investment' has caused and is now causing.
As for trusting a company to manage your boat, If they are like my rental agency, they are going to do sloppy work, perform poor upkeep if any and charge you well above average prices.
do what you want:
I just want you to know this is only going to be a yearly tax write off because, you are going to be loosing money.
Why not just use the standard tax deduction for a second home and save yourself all of the renter/ broker related headaches ?