Two Happy:
We have read a 9.9 kicker will not push the boat in a four knot and above current should we have an emergency with the one larger motor.
The efficiency of a kicker of 9.9 or 8 hp is determined by the size and pitch of the prop. Most 8 and 9.9 hp outboards (The 9,9 configuration is only because some lakes only allow motors less than 10 hp). have small prop diameters and a large pitch--which is fine what most folks do with these motors--they are used on small boats; dinghies or aluminum skiffs.
An 8 or 9.9 hp motor will push the C dory 22 at hull speed if properly equipped with a "big foot" or "sail drive" outboard--with a low pitch. An example I use often was my father's 26 foot sail boat--same hull form as a C Dory--arc bottom, no dead rise, and hard chine. Weight and windage were equal to a c Dory 25 or more- was easily driven to 6 knots with a 1932 5 hp Johnson outboard. So it is not the HP, but the way it is propped.
As to the 4 knot current--lets say that the kicker will push the boat at 5 to 6 knots, then you are making 1 to 2 knots over the bottom. I have been there in our Cal 46, where I had to get thru a pass, and the current was running over 6 knots, and the boat was capable of 8 knots under power. (we had to pick up our dog after surgery) Any boat is easily driven to the theoretical hull speed: sq root water line length x the constant 1.34. Lets say the C Dory22 has a LWL of 19' and the formula gives a speed of 5.8 knots. So if you can make 5.8 knots--you will be making 1.8 knots across the bottom into a 4 knot current. I see a kicker as a way of getting some steerage way on the boat, and getting to a safe place, where you can anchor until you sort out the issue with the main engine. We use a dinghy motor as a kicker--3.5 hp. Never worry about what speed, or going against a 4 knot current (even though we have done a lot of boating in the PNW). It would take a set of very unusual circumstances where you were forced to go against a 4 knot current. Most would go with the current and find a safe anchorage.
On the other hand, modern outboard motors are very reliable. I have been running outboards for slightly over 70 years. I have had one failure; there I still was able to get on to my destination under reduced power. That one failure was the oil pump on an early Fitch technology Evinrude 90 hp (2 stroke, direct oil injection to the crank shaft 1996 vintage). Looking at the thousands of miles the C Dory's go there are a hand full of stories of motor failure--one was a larger Honda where the thrust bearing gave out which lead to catastrophic failure. Good maintenance makes the modern outboard about as reliable as modern cars.
If you feel safer with twin motors--then go for that configuration. The most common problem with outboards is bad fuel. When you have a kicker, it is wise to have a separate fuel supply and separate starting mode--either a separate battery or hand start.