I've got my goals, I've joined a mastermind group for accountability, analyzing deals daily, now building my team, next step is make some offers and keep the ball rolling.

With all of that said, SO MANY properties that I have analyzed don't become the "good deal" without buying at a $10k discount (from what current list price is).So, when is it appropriate to put in offers at those kinds of low-ball numbers? 

Does anyone have any ball park numbers on how to estimate rehabs in dc...

But If I ever really just need a good accurate estimate I will call a realtor familiar with that area and that can do an estimated analysis to give you a good ball park value. 

I've been eye-balling these 2 cities and Madison seems to be terrible for cash flow..  

Then I have the advantage to low ball the offer and negotiate a really good price.

I will be targeting two areas; a fix & flip to pull out the cash when I re-finance or a multi-family home (2 or 4 units) to live in one unit and rent out others.I am considering partnering with a hard money lender on a deal to get the ball rolling...or should I just wait to save money myself?

More experienced flippers can ball park, but for your first few deals you will probably want to walk the deal with a GC to get your quote. 

If the property sits for a while and or higher bidders become unable to perform, they may circle back and ask if you want to re-bid or play ball and you are likely to get a decent deal then. 

This is crazy that they even have the balls to charge that much.