Hi Mark
I too have a Garmin 800, had it since Christmas and was like you in deliberating over the 800 or 500. In the end due to the offer that was on I went for the top unit plus a fitting kit and cadence/speed sensor for my 2nd bike.
Excellent piece of kit and I feel worth the extra over the 500. The touchscreen is flawless for me. I have dabbled with some of the features and have programmed it to do workouts on the turbo, which worked well. Easy to switch between bikes once you have tapped in all their details, HRM strap is very comfortable much better than my Polar one.
I cannot comment on the mapping/navigating as I have not used it to direct me on a ride. I aim to download the Mega Meon course I'm doing on to it to and check it against the directions given on the route arrows etc.
The Garmin Connect website is easy to use and this would be the same for either unit.
One thing to be aware of is that when and if you buy the 800 make sure it comes bundled with the City Navigator Europe NT SD Card as they do sell the unit without it. The basic maps on the standard unit are rubbish and to buy the CN card separately is a hideous price and makes the cost of the unit more expensive.
There is an Ordinance survey SD card bundle option which I believe would be be more suited to MTB navigation as the CN card is aimed more at road riding.
As for your HRM I assume it would pair up, but depending on which bundle you go for a HRM may come with it. I'm aware there is a new model on it's way, as for the differences I've not bothered to find out.
It might make the 800 cheaper though and give it a further edge (pun intended) over the 500.
Hope that helps, any more questions just post them up and I will try and respond.
Regards
Graham