We just bought a 2016 855 many many many thousands cheaper than an 895. With respect to your list:
Heater / AC - it had factory reverse cycle AC & heat but (as you point out) only useful on shorepower. Former owners actually ran a small Honda generator strapped to the port swim platform which is essentially inaccessible and not otherwise used. We're in Vancouver and have no need of the AC so have pulled the AC unit and installed a Webasto diesel furnace. Having spent some time on the Chesapeake, I understand an AC unit may come in handy much of the time. The portable generator may work for you.
(on a related note, if anyone is interested in a lightly used reverse-cycle AC/Heater unit perfectly suited to an 855, for a very good price, let me know!)
Generator - correct. With single mid-hull fuel tank, there is literally nowhere to put a generator. As above, the port side swim platform can be used temporarily when necessary. I think generators were reserved for later models with two out-board fuel tanks ... only 895s methinks.
Hot water - we have a factor installed 25 L (6.6 US Gallon) water heater with hot and cold running water in the galley and in the head sink/shower.
Bilge Pump - correct. Easy enough to swap out or install float switch.
No Microwave - correct. Stove and rod-holder mounted gas grill are perfect for us.
Leaks - ours is solid no leaks (we're in Vancouver ... it's been tested). One water ingress spot was the helm door. It didn't leak per se, but the drains in the door rails became obstructed with debris and water overflowed into the step just inside the door. Luckily it just pooled there and didn't go anywhere else (like mid cabin).
Vent issues - I read about these extensively before we bought our 855. The vent on ours appears to be positioned/designed differently than many that had issues - it is almost at the rub rail, and includes an anti-siphon vent. I think ours is a very late 855 where they rectified some design issues pre-895.
Outlets - this is a problem. The two outlets are not in great places. One is in the far back corner in the under-stove cupboards. The other is behind the water heater/pump access panel next to the battery charger in the mid cabin. We may change this. Also, there is only a single 12V outlet on the entire boat. I had USB outlets added to the dinette, mid and forward berths. Considering putting another 12v Outlet in the battery switch cabinet/area (for cockpit use) and relocating the AC switches to more accessible locations.
We have the Offshore version of the 855 with twin 200s. Love the on-water performance - decent fast cruise and good get up and go for a 30' family cruiser.