@Jason Stephens ,
Congratulations on taking your 1st step to financial freedom. Good luck!
You can find deals on the MLS but I think the catch is to move quicker than the other guys (or gals).
1. Have you thought about direct mail marketing, driving for $ or real estate auctions?
2. It is difficult (but not impossible) to find an agent that will actually do data mining. On average, agents gather criteria specified by you and then you'll receive automated messages for properties fitting your criteria. Tip: the properties listed on the MLS that need work are categorized as "Fixer Uppers" and an agent could run queries pulling off of this category.
3. This is reasonable but to be able to do a flip a month (which I haven't done yet) is persistence with offers every week and then setting up some sort of property tracking mechanism to follow up on properties you've made offers that might still be available.
There are trade offs with targeting properties where you're expecting to make $20K/property. If something comes up that is significant and unforeseen or if your ARV has changed based on market conditions (therefore causing you to reduce your selling price), there is a possibility that your profits are wiped out. If you target properties at higher ARVs (and therefore higher profits), you do have more cushion (dollar for dollar) for those unexpected costs.
You always stick to your numbers. The trick is what are the underlying assumptions for those numbers. If I'm looking at a property that has 3+ comps that are identical, DOM are short, desirable school district, nice location etc. etc. then I might increase my ARV to the higher end of the range and reduce my holding period (thereby reducing my holding cost). And vice versa.
Good luck and excited to hear about your success!