Does owning outdated equipment actually lower my price, or just complicate the deal?

Often both, though in different ways. On price, outdated equipment can lower what a buyer is willing to pay if replacing or upgrading it is something they'll need to budget for shortly after closing — that expected future cost gets factored into their offer even though you're not the one who will incur it. On complexity, outdated equipment can also slow down the deal itself, since a buyer's advisors will want it identified, its condition assessed, and its value, if any, reflected accurately in an asset sale, rather than simply assumed to be worth its original purchase price.

The nuance is that "outdated" doesn't always mean "worthless" — equipment can be old but well-maintained and still fully functional for the business's needs, and a buyer's own view of how much longer it will last matters more than its age on paper. Conversely, equipment that looks fine but is close to needing replacement is a bigger risk to a buyer than obviously old equipment they've already priced in.

Getting an honest, current assessment of your equipment's condition and remaining useful life before you list, rather than relying on what you originally paid for it, helps you and a business lawyer present the asset picture accurately instead of having a buyer's inspection set the narrative.