Nice post, rocheyb.
Slight aside, but I love how diverse the playing approaches can be. Personally, I usually start a save for a particular club. I don't use the journeyman style but it has its appeals. With the specific club, I usually try to gradually evolve it to where I want it. But wholesale, mass changes is something I have avoided. It makes sense, though. I really like the thought of starting unemployed, simming until May and seeing how got relegated, then taking over and making it your own. I've only managed in the Championship a few times but its almost always been with clubs that were relegated the season before and have a strong squad (at least for that level).
Things definitely click on another level when you have the right players for the tactical approach you want to use.
Regarding scouting players, one of my favorite techniques is to target players from big clubs. The big English clubs, Barcelona, Real Madrid, Atletico, Bayern, Juventus, Dortmund.... They all tend to both buy young prospects and spend big on fully developed stars. These two purchasing approaches create problems - someone isn't going to get matches. Whether its an established star keeping out the new signing out, the new star pushing the current player down the pecking order, or the prospect not getting a chance.... someone is going to be unhappy and potentially expendable. mid level Prem clubs have done this for a while, picking up "failed" players who came thru the youth system at United, Arsenal, Liverpool, etc, and turning them into solid Prem level players. The downside is because they are at big clubs, they are often on a decent wage and if you are small, they may not be interested whether you can afford them or not. But its worth keeping an eye on the bigger clubs.
On my two most recent saves, Marco van Ginkel is back at Chelsea (think he's injured IRL but its not in the data update) and not getting any matches. They have him listed for loan. He's a good player, not a great one. Suffers for his versatility as he's not really specialized. Fairly high wage but Chelsea might eat that if you loan him. He never got loaned, then was transfer listed in season 2. Fairly high but they might negotiate. An example of a player who would be very useful for a recently promoted or even mid-level Prem club.
Another thing to consider - retraining. Generally, retraining someone to play another position is going to take a few months, if they have decent versatility and get matches there. So I you can't find the right creative forward, starting looking for AMCs, wingers, and even MCs with the right skills and just retrain them. It might be easier to find a solid DC who can be retrained to DM than the DM with the exact right physical attributes you want, I find.