>>>...Deciding btwn poolside and cliffside. Poolside is cheaper, so leaning towards that - but is the view/room still good?...<<<
The '..Poolside..' category rooms at The Reefs are situated right 'round the hotel's small, horizonless swimming pool. This area can act a bit like an '..amphitheater..' and amplify ambient sound (particularly at ground-level). This probably isn't a problem at night but during the day these rooms can be '..noisier..' than the '..Cliffside..' category rooms. All of the rooms will have wonderful ocean views...but 'Cliffside' views will be almost entirely un-obstructed.
The Reefs Resort & Club Map/Diagram--
>>>...I read that the restaurants sometimes close for weddings/private events. are there always good options open?...<<<
There's no accounting for whether there will be any 'special events' during your stay...but there are three(3) on-premises dining option at The Reefs at this time of the year--Ocean Echo (indoor & outdoor terrace) Coconuts (outdoor) and Royston's (indoor). All of the choices are good with varied menus. It will simply comes down to which you happen to prefer most/best. Given that June is perhaps the most heavily reserved month of the year for popular properties like The Reefs, probably the only potential problem you may experience is getting a table, at the restaurant your prefer, for the time that you prefer. The Reefs' MAP guests will ALWAYS be accommodated at its on-premises restaurants.. You might also consider participating in the reciprocal (table space available basis) '..Dine Around..' option with Cambridge Beaches and Pompano Beach Club.
>>>...our first time to Bermuda, do you recommend staying at the resort the whole time since it's such a short stay - or should we venture out to another area for an afternoon...<<<
The Reefs is your '..hotel..'. BERMUDA is your '..resort..' As pleasant as The Reefs is (and that's pretty damned PLEASANT), if you don't get out 'n about to see, experience and enjoy RESORT BERMUDA during even such a brief visit....you'll be sorry.