I think the first thing you need to do is narrow down your search by identifying exact what type of investment you are pursuing and then study the crap out of very specific sub markets.

She can take full advantage of the 121 primary residence exemption and take $250K of the profit tax free. 

In the meantime I am positioning myself by studying online to take and get my RE license, pursuing a managerial position w/Federal Civil Service to supplement my pension.

Total Profit if Sold: I just can't seem to get the numbers right!

Would urge you to develop your knowledge and firm up your investment criteria before deciding what route to pursue.

Boot is what the IRS calls profit that you take from the sale. 

Look for a minimum of $20,000 profit per flip.

I am thinking my strategy should be to approach a family member to lend me the money for a down payment and then take out a hard money loan and either do a profit share with the family member or 10% interest or something like that. 

if the Market Cap rate for this property is lower then yours by at list 2% you have some build up equity and could possible sell at profit.

Are there times where people have and have not pursued this technique?