The '06 heads were much improved on the exhaust side; lower floor and larger port; intake valve is a tad larger but the exhaust side is where the real improvement was made. The later heads flow much better than stock and for someone looking to do a budget build, they fit the bill

No, most machine shops wil charge about $100 to CC and deck cylinder heads. Decking .020" to .030", with a .030" head gasket, would get you the compression most bolt in cams would need but the exact chamber volume required to produce a specific compression ratio should be calculated.

SE cast flat top pistons run about $175 from the dealer but can be ordered online from a discount dealer like Zanotti's for about $130. The machine shop will need the pistons to bore and hone to fit; boring will run about $125.

You should be able to keep the parts cost under $1750. Shop Ebay for cams and buy pistons, lifters and pushrods from an online H-D discount dealer and that might save you a bill. In my neck of the woods, you can expect to pay $65-$75/hour for labor. If you have any mechanical skills, a service manual, a parts manual and are motivated to save a few hundred bucks, you should consider doing the work yourself; it's not that difficult.

Yes you can still tour with the bike; touring will be more fun with the additional torque.

The kit price quoted is not a fair price for what you get but does not address a cam plate/tensioner upgrade. You could simply replace the tensioner pads but if you can afford the later model cam plate, upgraded oil pump, hydraulic tensioners and roller chains, the upgrade is well worth the cost.

Never mind that what you may spend is 20% of the bike's value. The value is what the extra performance is worth to you; kind of like the Mastercard commercial; priceless!