I'll try to give you some useful advice, others may disagree, however these work for me.
1) Allowing that you may have a bad scout, signing a 36 year old is rarely a good idea. Particularly for more than one year. Let these guys go, then see who is available during FA. If you lack funds, wait until the Winter Meetings to go after folks. If they are still expensive wait until everyone is re-scouted on 12/31. Many players drop or increase at that time or on 1/31 (not sure if this is still a valid date in OOTP14 and later). You can still pickup decent players at this time, not stars.
2) Read up on the star system, it is not all that intuitive. However players do drop (particularly after nasty injuries) and bad years. Don't get overly reliant on stars.
3) Stamina is the least needed rating for a starter once he meets minimum requirements. These will depend on which rating system you use, so I can't give you a flat answer, other than a 'yellow' number (most of the time).
4) Player history, I guess. Not something I look at myself.
5) You won't die a horrible death if you let the AI set your lineups and rotation, however you CAN do better. Learning how is the biggest point of the game and there are too many little things to mention in a quick post.
6) Lots of player drafting strategies out there. The ones I use are:
Position players: sort by fielding position rating and then look for decent contact, eye and power potential. The thought here is that getting a player who can help you with a glove is a solid start. Then hope for random improvements in hitting so he's at least average will give you a solid player.
Pitching: I look for control and high ground ball percentage, then take whatever else I can get. Again random talent bumps and randomly developing another pitch can make a huge difference.
7) Resign all your coaches yourself. Around mid-year look at all your coaches and decide who is worthy of a renewal. Let the other guys walk. When they walk, you'll get an email. Go out and replace him then.
Works for me.
Hope that helps and you enjoy the game. There's a lot of good advice and even more terrible advice in this board, so read up.
And play, mostly play.
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"My name will live forever" - Anonymous
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