Do I need to make a deal on all three, closing simultaneously?

If both events happened simultaneously, I could cover them without dipping into my personal funds or pulling out the credit card.

You need a Title Company that understands "simultaneous closings"...

Depending on your state you may get an eviction and a cash judgement against her simultaneously, or you may have to sue separately for damages.

@Jeremy TaylorWhen the REO wholesale deal is nonassignable, it's easier to do a simultaneous close.

Now obviously I dont say, " I am going to do a simultaneous closing and make $50,000 as soon as we close hahaha!"

Todd,That strategy works great, as long as you can find an investor friendly title company in your area that will do simultaneous closings.

I plan to simultaneously build my buyers list while finding good deals.

Simultaneously, get involved in the forums.  

Code | US Law | LII / Legal Information Institute (cornell.edu)(2)Trade or business and investment propertyIf a taxpayer’s property held for productive use in a trade or business or for investment is located in a disaster area and is compulsorily or involuntarily converted as a result of a federally declared disaster, tangible property of a type held for productive use in a trade or business shall be treated for purposes of subsection (a) as property similar or related in service or use to the property so converted.The casualty loss is for property under 165.The replacement of the casualty loss property is under 1033.The insurance proceeds simultaneously reduce the loss under 165 while acting to create basis in the replacement property that will be recovered over future periods under 1033.