The way I read your question you are asking three things about how these impact chances of recovery - dosage, time on, choice of drug.
I'll give you my take, in brief they all do have an impact and you can improve your chances by understanding them.
Dosage - this one is key in terms of time for blood levels to bleed back down after you stop injecting. Short esters are so fast they are completely gone in two weeks, long esters may take many many weeks, and it gets worse depending on dosage. Take boldenone undecylenate which is one of the longest at 15 days half life. If you inject 600 mg/wk you are looking at six weeks post last injection to bleed down to lower blood levels than your natural test production. So dosage is critical, particularly with long esters. Timing for PCT on these is also key.
Time on - I read a study recently where they state a cycle length of 12 weeks shows the vast majority recovery very well with a good PCT. Any time longer than that it gets more difficult and less certain. You'll see lots of guys go with 14 to 16 for longer esters. In a case like that I think it is critical to keep the boys working by using HCG in meaningful doses, 2 x 250 IU pw is bare minimum 2 x 500 IU pw is better.
Chemical - choice of the drug matters in terms of impacts to other hormones - like for example aromatizing drugs can drive your estrogen crazy which if not managed can cause all kinds of sides, and might impact eventual recovery. Another is 19-nors than can boost progesterones and in the presence of estrogen boost prolactin. Getting those other hormones way out of whack might impact recovery, or lead to nasty sides afterwards. And finally deca for example has metabolites that hang around a long time and also inhibit recovery - so doubly whammy with long ester so long time to bleed down, and metabolites that hang around even longer. If you use deca make sure you run the test several half lives longer, like say four weeks would be good, before you try to recover.