The ADA question killed the margin on a concierge and transport service
Two properties, 190 and 155 units, both marketed as independent living lite. Age-restricted, no personal care, but with a package that included scheduled transport, a concierge desk, and light errand support. The operator wanted it outsourced and I bid it. Won both on a per-unit fee, $47 per occupied unit per month, so roughly $195k a year across the two properties at their occupancy.
My transport model was two 14-passenger shuttles running fixed routes, grocery twice a week, medical appointments three mornings, and a Saturday social run. Priced on drivers, fuel, maintenance, and a lease on the vehicles.
What I did not price: accessibility. About four months in I had residents who use wheelchairs and walkers, which in a community serving people in their late seventies and eighties is completely predictable and I somehow treated as an edge case. Retrofitting a lift into a leased shuttle was not permitted under the lease, so I ended up chartering wheelchair-accessible vans on demand at $180 to $240 per trip. In month seven that was 38 chartered trips. Roughly $7,600 in a month against a total revenue of about $16,200 for both properties.
By month eleven I was running negative on the transport component and subsidizing it out of the concierge fee. I renegotiated at month fourteen, went to $61 per occupied unit with a separately billed accessible-trip pass-through, and lost the smaller property in the process because their budget wouldn't take it.
Direct cost of the mistake was about $58k of margin over fourteen months plus the lost contract.
Whether transport of this kind triggers specific accessibility obligations depends on how the service is structured and on state and local rules, and I should have had a lawyer look at it before I priced anything. I didn't. That's the actual error.
What I'd do differently: assume an accessible-trip percentage from day one, price it as its own line, and put the vehicle spec in the bid rather than the vehicle lease.