I think the question that hasn’t yet been asked by your friend or any other respondent is – how much would it cost to rent a comparable trailer vs. buy this one AND rent the pad? Comparing the purchase / rent cost of a trailer to a property that rents for $1650 per month is just wrong.

I mean, if the guy is willing to live in a trailer to save money, seems like renting a trailer is the way to go. The cost difference will be pure after-tax savings and he has no depreciation concerns.

What he really needs to do to lower his taxes is incorporate and become a contract employee and write off stuff that he can’t write-off now.