Answer:
1) a. True
Rosa is almost always right when she knows that her company is a monopoly, i.e. has no competition, but is generally wrong when her company has to compete with other contractors. It is simple, a monopolist can decide which markup percentage to use, and can use a really high one, but when competition exists, markups are not so high and profits not so abundant. That is why she almost always gets it wrong when having to deal with other competitors.
2) a. False
The winner's curse usually happens when someone wins a bid over some contract or asset, but then they realize that the actual price of the contract or asset was lower than the bid. E.g. in an auction, two people are fighting over to see who buys an antique car which increases the price of the car way beyond the real market value. But it can also happen to a company that offers very low prices, and then after they won a contract, cannot perform properly because their actual costs are higher.
When a company makes an offer, they are certain about the price of the contract and they should know the value of the services or goods that they are offering. If Rosa underestimates her costs, and prepares her offer using unrealistically low costs, then she will probably win the bid but end up losing money.