I responded to some of your questions in another thread, but thought I'd contribute here too. My answers are listed after your questions, which are in quotes below.
Even though I can feel my body wanting and needing the extra fat, will I put fat on while going from a moderate carb/fat/protein diet (currently) to a ketogenic diet as the body adapts to fat burning or will the shift just be apparent in some initial fatigue? I just don't want to take any steps backwards and gain more fat while trying to shed it.
If you are getting most of your calories from fat it's terribly hard for your body to store fat away. The biochemistry just doesn't favor it. A bigger question is whether or not you can meet your stated goals while staying ketogenic. Anaerobic workouts (like weight lifting) favor the burning of glucose, so if you aren't eating foods that can provide this glucose then there's a high likelihood that your body will start cannibalizing its stores of protein (aka muscle fiber) to turn into glucose through the process of gluconeogenesis. The end result is that you'll plateau in terms of your athletic goals and your physique even as you continue working out. I think you're much better off eating a modest amount of carbs, say 30-40 percent of your total calories. A ketogenic diet would be great if you were training to be an endurance athlete (i.e. doing aerobic exercise like long gentle runs or bike rides), but it doesn't work that well for anaerobic athleticism, in my experience.
I also don't see why you want to stay in calorie deficit. If you're working out hard, that is not the time to attempt a calorie restricted diet provided the calories you're eating are nutritionally useful.
-Will the 20-50g of carbs allow me to stay in ketosis?
Yes, but see above. I think you are undermining your training goals by trying to stay ketogenic.
-When would the best time to consume those carbs be...post-workout or right before bed to fuel the fasted workout?
I'd eat them about an hour before your workout, or right before bed if you intend to go into your workout fasted.
-How long does it take to get into ketosis?
It varies from person-to-person, and on whether you've been ketoadapted before. I'd guess 2-4 weeks.
-What can I expect as far as training while on a keto-diet?
If you're doing aerobic training (gentle running, swimming, biking) then you will see slow but steady gains over a period of 3-6 months, then slower gains for perhaps the next few years as you ease towards your full potential. Your endurance will become amazing though, as long as you keep your heart rate low enough during exercise that your muscles remain in aerobic territory. On the other hand, if you're doing anaerobic training (sprints, weight lifting, CrossFit) you will feel terrible, and you might even pass out. Your strength gains will be far below potential and you'll probably plateau reasonably quickly, and you'll have trouble gaining muscle mass because your body will constantly cannibalize muscle tissue to turn into glucose. If your main workout regimen includes anything anaerobic, including weight training, I strongly advise against attempting to stay in ketosis. There is definitely a time for this style of eating and metabolism, but it's not for stretches where you're doing a lot of anaerobic work.
-How long does it generally take for the body to adjust to a keto-diet? Any cons of entering ketosis?
2-4 weeks, in my experience. The only con is that you feel terrible for a while, but that passes. See my above comments about attempting to maintain an anaerobic training regimen while in ketosis though. Not recommended!
-Is a keto-diet optimal for cutting to the bodyfat percentage goal that I have or could I reach my goals while still consuming carbs?
I can't say whether it's optimal, but it can definitely work if coupled with aerobic workouts. If your goal is to do anaerobic workouts (weight lifting), I suggest more like a zone diet that advocates a 40-30-30 balance of carbs-protein-fat. When I first started CrossFit I tried desperately to stay in ketosis, and it was an epic fail. Only since transitioning towards more moderate amounts of carbs has my body adjusted to the rigors of CrossFit (and anaerobic training more generally). Since I transitioned, strength gains, lean muscle mass gains, and body fat loss have been swift.