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I'm wondering is this really a cost effective investment?

You will take advantage of the primary residence exemption twice and the second time will have the effect of turning of the tax deferred dollars into tax free dollars.  

I had no clue it had a ripple effect in a sense of it being connected to Trip Advisor.

I know it's a very good idea to have it (although not required by law) but I'm not sure I understand it.In what instances would Title Insurance come into effect?  

Will this effect anything?

I've seen some discussions on staying away from HOA's but how does that effect the purchase of a PN?

I know a lot goes into selection of neighborhood, floor plans, schools, etc. but on a more macro scale what measure can be used.

The IRS generally agrees, and their audit guidelines specifically address a situation where someone own only a few rentals and tries to claim this status.And, as discussed above, that depreciation deduction is reducing your basis, which has the effect of increasing your gain when you sell.  

But, the fact that the daughter has been paying the real estate taxes for 5 years could also have an effect on the legal status.