Details: North SJ, near the future BART station, town home, 2BD/2.5BA - 2 master bed rooms, low HOA and well maintained, near future developments and another town home complex to be built nearby, ~1100 sq. feet, decent school district (Piedmont High School, 4/5, 10/10 on Redfin), 1 car garage and 1 carport w/a private patio, close to Target and other shopping areas, laundry downstairs and in the building.

One strategy would be to create a metrix to identify those properties of yours that would yield the greatest amount of cash but have the least gain and that you've owned for the shortest time (but still over a year so the gain is capital not ordinary income) so that your depreciation recapture is minimized.

The work included replumbing the entire home, new furnace and A/C, new water heater, Lower level gut and refinish, new patio, new garage door and garage repairs, new roof, kitchen gut, bathroom gut, hardwood refinish, new flooring, new doors, new trim, a lot of drywall work and paint.

Given your W2 income, early withdraws from those accounts will likely kill you (its taxed at your ordinary income level plus a 10% withdraw penalty).  

I am not sure but I guess that works.. trying to get folks to think your just an ordinary Joe.5.

@Amanda Malson,As a general rule, flip income is ordinary self-employment income, not capital gains.  

To really get on their good side, you can also provide a gas grill for cooking out with patio furniture.

Hello,I have a 2650 square foot, two-story home (4 bedrooms/two bath) that needs a complete remodel and upgrade, inside and out, plus a new patio cover.

If the numbers are attractive, what would you do - filling it or "flip" a pool (maybe the patio walkways, bricks, and fencing around it?) 

Either way, if you flip houses that is ordinary income.