If we sell investment Condo to convert to primary 2 years later to use tax exclusion and protect gain during investment years will the post 2009 "non qualifying" years (rental) be excluded from protected gain?

Depreciation (excluding the land value) is based on your costs to acquire (basis), not on the market value.

subsurface water issues excluded. but if you had a bunch of subsurface water issue the pool would have popped up out of the ground by now.

Also, even if not direct collateral I can't even find anyone who considers them assets, its kind of like money that is just excluded from most asset calculatipons. 

No where is it more over rated than in real estate sales, excluding sports, politics and religion. 

Patch in all siding, trim and fascia as needed Repair all cracked mortar in brick areas Replace single panes of glass at all broken windows Reseal all exterior windows and doors Paint all siding and trim - excludes brick. 1 siding color and 1 trim color Patch and seal roof in all necessary areas Electrical: Update panel box to Code HVAC: Install condensor unit and concrete pad InteriorDemo all interior - Flooring, trim, countertops, bath fixtures, electrical receptacles, etc.

There's a little more to it, but for starters put all your rehab costs on line 19 "see statement 1" of Schedule E, broken down and itemized in a way that I can line up one-time expenses with invoices for $x, $y, and $z that line up perfectly with "see statement 1" to exclude those expenses from DTI.There's no reason you can't get preapproved for that refinance prior to purchasing the place hard money.

All of the gain would be excludible.  

That's a 4-5k fix excluding painting, that's LA price and you know how that's overrated.

An automatic six-month extension from the due date of the return, excluding extensions (i.e., generally to October 15) applies for individuals who have filed their tax returns by their tax return due dates plus extensions (Announcement 99-57 and Treas.