When you say a couple people, do you literally mean 2? I think you can get away with a regular Uber/Lyft at that point because suit case(s) that don't fit in the trunk can ride on the bench seat next to one passenger, with the other in the front passenger seat.
Once you have 3-4 people riding, though, it can be a toss up depending on the size of the driver's trunk and how empty it is. Our family of 5 has rented full size sedans with 2 medium rollers and 2 carry on size rollers. We are able to get them into an empty trunk: it's a toss up whether we can fit personal items in there or whether they have to ride on our laps. With ride share, you may not be looking at a compact and then the trunk space may not be sufficient for 4 suitcases.