If it was me I'd talk them up-sell to 4-5 apps...and clearly explain that 3 apps is the bare minimum company standard. Even offer that the app today is free if they sign up for 5 apps now!... again explain the benefits and guarantees that they would get for the up-sell...(cuz I'd be/you'de be there doing the re-spray either way) The boss says to go re-spray to cover customer service in a sense in the hopes of securing the HOA sale for next year. Two backyards is a small cost compared to the HOA in his rational (assuming the financials approve of this). EVEN MORE so if your company currently does the apps and mowing for the HOA...If your boss is a subcontractor to the mowing company then boss-man might be softening up potential clients as he's looking to expand/ sell more houses next year and it would make those new sales easier if the neighbors didn't complain by coming back and "fixing" Sall Sue's property.