I wouldn't. Save the money on the NGC membership. Get an ANA membership if you don't have one. It's cheaper than NGC but you still can submit to NGC (just no free coupons).
I would not either. IMO a coin should be worth around $100 min before getting it graded. If it is worth less then sell it or trade it for one that is graded when you get it.
Problem with that is once it's graded it sells for more than redbook. Hard to find $100+ coins in the raw that have not been graded already.
Most of the time for coins that aren't really commonly found as counterfeits or coins in really high grades (AU58+), the cost of grading matches the difference in price, so you break out even. Just my personal experience.... Also, at every major show and even the small shows in small cities by me with only 10-12 dealers, most of the coins are raw and also quite costly. I bought a proof indian cent for $225 raw.
Take for instance a 1859 Seated Quarter. Value is $45 Red Book in VF-20. Cheapest I can find one on the net slabbed by NGC is $99.
#1 (maybe)...forget about the rest. They're all nice coins...but not ready for the TPG investment (imho).
I would go ahead and wait until you got some really super coins to have graded. The ones that you presented are not TPG material. Maybe some nice MS65 Morgans, some Barbers or some Indian Head Cents. If I had to choose as to which I would send in I'd go with item number 1, then item number 5 and finally item number 3.
For the most part that looks like a good candidate. I think that the suggestion of $100 or more book value is good, if not more than that. In the end though it comes down to what you want in your collection and how you want it stored/presented. If you're a slab person, slab it.
Back in the '70s...when I last collected, the rule-of-thumb was that you could expect to get "on average" 50% of Red Book when selling anything. Of course, this was before TPG and eBay.