Dick, I went thru this same exercise in 2017/18. Looked at the same boats plus several others that were in the similar size and style (cruising). We ended up going with an Endurance 658 vs the Fleming 65, Outer Reef 65, Offshore 62/64, Grand Banks 60 and Nordhavn 60. My wife and I primarily cruise together with occasional guests so being able to handle the boat with just the 2 of us was paramount and we developed a list of about 25 "must have" items/functions in our search/selection of a new boat. We have friends who have Flemings and Outer Reef 65 so my comments are based on observations during our search plus having spent some time on our friends boats. So with that said, here are my thoughts:
Fit and finish were about equal. Fleming had a little more of serious cruising finishes/touches in PH and Galley.
Engine room head clearance and access were better in Endurance (I'm 6-2, not real flexible and do most of my own minor maintenance and repairs). Finish in ER, bilge and Laz is nicer on the Endurance
Master Stateroom is in the bow on the Fleming. We required mid ship so this impacted our final decision.
A lot of exterior teak, something I had on my previous boats and wanted to get away from. My friend pays around $5-8k annually to have his teak maintained/varnished
Interior is very traditional which is neither good or bad but personal choice. We plan to spend 4-5 months a year on our boat and wanted more of a "home" feel and little more contemporary styling
Did not have room for double stidd/captain chairs at pilot house (and maybe fly bridge but not sure). Standard on the Endurance
The Fleming 65 is 72-73 LOA vs the 658 is 68 LOA-this had an impact on the slip we could get (a lot more 65' slips than 70' slips are available in our area)
The salon/galley/ph were more separated zones vs the open plan of the Endurance
Ride-I have only been a passenger on the Fleming in seas of 5-7 feet on 8-10 seconds. Based on similar sea state on our Endurance, ride feels the same. Both boats punch thru seas and do not slam when coming off waves. I have had my Endurance in 8-10 feet on 8-10 seconds with 20 kts wind and the ride was the same.
Fleming has less windage and lower profile which could have impact on docking during windy conditions. We addressed that with getting larger bow/stern thrusters than are on the Fleming
They tend to have smaller HP engines for similar size boat. Both boats burn about the same fuel at same speed but I wanted ability to travel faster in case of emergency or weather issues.
Fit and finish is lower than Endurance
Based on my friends boat, they seem to have more system issues than I have experienced on my previous boats. I would say they use "B" grade system components and Endurance and Fleming use "A" grade.
They have a lower price point than either boat and probably for a reason
Did not have room for double stidd/captain chairs at pilot house and fly bridge.
We plan to do most of our boating on the west coast and Outer Reef did not have any real presence or support in this area. They are primarily located on the east coast. Since we purchased our boat, they have added a dealer in WA and have one relatively new boat in the area. Hampton/Endurance has better support and service.
Engine room head clearance is ok but not as good as Endurance
Hope this helps and keep in mind this is just my opinion. YMMV