Search for appnotes on the subject; there's a lot of info out there, especially regarding power packages (exposed pad types and etc.).
You can do via-in-pad, but the vias slurp up solder, which is a bad idea for manufacturing with paste and reflow. I suppose you'll be hand soldering these anyway, so just add solder until there's a neat fillet around everything; if it's oozing out through the vias, it's probably a good thing (more metal!).
You can place vias around the perimeter of the footprint, so there is no exposed soldermask connecting them to the pad. This puts more copper between heat source and sink though. You can't expect much out of an SMD part anyway, so the ring-of-vias method is pretty good.
Use vias you are comfortable with, big enough and numerous enough to do the job. I would say, use no less than the amount of copper connecting to the pad:
Suppose the pad is square, 10 mm on a side. That's 40mm perimeter. Suppose the board is 35um stock, plated to 70um (2 oz. finished foil thickness), with 35um via wall thickness. That 40mm perimeter is in 2oz. but the vias are 1, so you need 80mm worth of via perimeter to equal that. A 0.5 mm via has 1.57 mm circumference, so you'd need on the order of 50 vias to equal that.
You can make whatever excuses you like: the backside copper pour will only dissipate half the power (ideally speaking), so it doesn't need the same cross section as the footprint itself. So 25 vias. Maybe you don't need as low a thermal resistance -- PCB heatsinking sucks anyway, and a 50 mm square region isn't going to handle more than a few watts before it's too hot to deal with. You won't loose *too* much by skimping on vias here.
Normally, I go with 20 mil vias, spaced 40-60 mil apart, in rows, along three or all four sides of the pad. For a D2PAK, maybe 6-8 per side, or 18-32 total.
Follow the manufacturer's requirements on design rules, spacing, etc. Usually you can't put holes closer than 10 mil, edge to edge; EDA tools usually flag putting a hole through another component's copper, or overlapping shapes, so that a 20 mil via can't be spaced closer than 30-60 mil depending on annular ring (if specified, or if derived from design rules). Assuming you obey the DFM checks that is.
Tim