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Hey shortstacked. Sorry I haven't had a chance to reply too much in your threads. Don't get too down; we all run into rough patches. And if it's better for your pysche to cash out, then by all means do so. Better to keep the money you earned than lose money, right? 
As far as learning, DON'T GO TO COVERS!!! That is one of the worst places I know of to learn. They feed you blatant misinformation and their articles are (to say the least) pieces of crap. Honestly, I sometimes think that they post things to encourage their users to lose (as they work off of affiliate fees). DO NOT LEARN SPORTSBETTING AT COVERS!!!
As for betting early, that's up to everyone's discretion. Personally, I find I get completely owned on all my 'first impulses', picking like a sorry 20-30% (indeed it would probably be better to fade my 'early leans' ). However, maybe picking early works for you. I know at least a few handicappers who do so. Just find what works.
I factor in where the public is on a certain game a lot into my bets now (whereas I used to basically ignore it). I feel that it gives a lot of insight, and so that's why I usually wait until later to bet.
Doing what you're doing with 'play money' is very smart of you. I know of very few handicappers who are disciplined enough to do that. By doing so, you can see whether or not you really want to pursue this (and just how expensive or inexpensive it will be). Kudos to you for doing so.
If you ever have any questions, just ask. I (and I'm sure everyone else here at FTR) am more than happy to help.
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