- If you pick up someone like Wainwright or Strasburg in August, for example, and want to keep them for next year, would you be allowed to? It seems unfair that someone can just pick up someone like that and only have to sacrifice their last pick of the draft next year to keep him.
No, absolutely not, it would be completely unfair and should immediately be ruled out.
- This leads into the next question, can you only keep players that were drafted the year before? Or should we implement a deadline during the season for which you can add someone that you intend on keeping?
You cannot add anyone and keep them. It makes no sense. You draft them and are allowed to keep them for a draft pick equal to the round in which they were drafted, period. If you do not draft them, they are not able to be kept. If you want Strasburg or Wainwright then draft them, heck of deal since they will not be in the top 5 rounds. Personally, I would say anyone slated right now to miss more than a month is off limits and eliminate this loophole. That said, it could be interesting to see who uses a much earlier pick than they would have otherwise.
- Question 3, if you trade for someone that was drafted in the 3rd round for example, and you want to keep someone on your team that you drafted in the 3rd round yourself, how do you keep both players?
You cannot keep someone that you trade for. You can only keep someone you drafted and can only keep them if you give up a draft pick equal to the pick the cost to obtain him. If you must not follow this suggestion, then I would say that it costs the next round pick. So, in the scenario your presented it would cost their 4th round pick, or do the opposite and say round earlier making the pick the 2nd.