When two boats share the same hull type — in this case both the Pro-Line 20 Express 2008 and the Pro-Line 29 Grand Sport 2013 are modified vee designs with fiberglass construction — the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?

Size is the most obvious dividing line here. The Pro-Line 29 Grand Sport 2013 measures 29,3 feet overall (2013), giving it roughly 27,3 additional feet of deck space compared to the Pro-Line 20 Express 2008 at 2,0 feet (2008). Weight tells a clearer story for trailering families: the Pro-Line 29 Grand Sport 2013 tips the scales at 631 lbs — 356 lbs less than the Pro-Line 20 Express 2008 at 275 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.

The power gap is worth calling out. Rated to 600 hp, the Pro-Line 29 Grand Sport 2013 has a 400-hp advantage over the Pro-Line 20 Express 2008's 200-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Pro-Line 29 Grand Sport 2013 carries 24 gallons versus 7 gallons in the Pro-Line 20 Express 2008. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.

For family outings this is probably the sharpest distinction between the two. The Pro-Line 29 Grand Sport 2013 is rated for 8 passengers, while the Pro-Line 20 Express 2008 caps at 6. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Pro-Line 29 Grand Sport 2013 could be the deciding factor.