Hello Again Christine!
I'm glad you're finding my suggestions useful ... and I do hope that you act SOON on the one VITAL aspect -- booking that Naxos-ATH flight. If you worry about "tweaking", Aegean provides for a flight-change ... but if you do NOT get that flight, the whole plan goes sideways. So do not dither, Please! So often, people get all absorbed in hotels, when how to get there is the First Concern.
RE: Hotel recommendations -- Again, how to give useful advice on inadequate info??? I would need to know your preferred budget range (in Euros please - use http://www.xe.com/currencyconverter/ ) ... and also, your travel-style (aside from $$) , superbudget, economy-moderate, or indulgent. Do u like lots of staff in uniforms? Want a spa? Need a pool? View? Or just nice rooms, being out/about a lot? Examples:
• NAXOS – in June I always recommend staying on Ag. Giorgios Beach directly adjacent to the Port town; because SO handy just to stroll in for cafes, dinner, nightlife, or to get bus for far-out beaches -- no need for car except when u want to explore around the island. However Ag. G has only 3 "upscale" hotels and their location isn't as good as some simpler places. Often people ask me about posh places with glam websites ... which in actuality are way back from a beach, isolated, require car rental even to get a cup of coffee. But these people are going by "smart-phone research" instead of some real homework.
•SANTORINI – the big push is for Oia by the super-luxe crowd, bridezillas, others affected by promo... and indeed it does have the superluxe places. However, I like Firostephani best .. it has hotels with great caldera views, pools etc, at half the price -- and it isn't jammed from 10am - 4pm, 6pm-sundown with cruise crowds, package-tour throngs etc... in fact no one stops at Firostephani except the smart few who book rooms there. My routine, with newbies like u, is to catch the 8:15 bus to Oia (a handy Firostephani stop just behind the rim-side hotels), and enjoy Oia views & take pix early, before the human "rush hour". But that may not be for you... its just my opinion, based on 5-6 visits to Santorini, I forget which.
You say you're open to opinion & information, now I suggest you get some by reading. Websites (except for those like VisitNafplio), often have a promotional motive OR don't provide CANDID guidance. Just for example, you wanted Meteora, but weren't given guidance on whether it made sense on your timetable.
A good guidebook saves you time & helps good decisions, by filtering out static. I emphasize GOOD (a well-known series was unmasked for an editor doing a complete country update without leaving NYC!). I believe anyone spending $5K+ on a vacation should pop for $10-20 for a guide... or at least borrow a bunch from the library & photocopy relevant pages. I have a shelf-full, but mainly recommend ROUGH GUIDE to GREECE, not necessarily the newest edition; you're not looking for latest hotel/dinner prices, but for honest overview & background fax. Used 2012 ed on Amazon for $5 or so + shipping. One great feature is that you don't have to take along the Big Fat guide; pull out sections (Peloponnese, Athens etc), bind spines w duct tape and -- Voila!! - little pocket "guide-ettes."