Does the $10000 cap on property tax for homeowners count towards the $27000 figure? How about out of pocket medical bills ? Insurance premiums? charity?

[Opus 17]

The $10,000 cap is for the deduction of "state and local taxes."  That includes property taxes, state income taxes or state sales taxes (depending on your state), and certain personal property taxes in some states.  

Medical expenses are subject to the 7.5% "floor" but are not capped.  

Charity donations are not capped, but they are subject to the usual 20%/30%/60% rules.  (Donations that are very large relative to your income may be capped and the excess carried forward to next year.)

The overall schedule A itemized deductions will also start to be reduced at very high income levels, there is a phase out formula but it is not severe.