I feel that one of the conditions of being able to establish a mainline 'connection' is that the railway concerned then agrees to participate under the delay repay scheme. Say for instance I am travelling from Ropley to Newcastle splitting my ticket at Alton, i.e I purchase a Ropley to Alton first class single for travel on the Mid Hants Railway and then a separate first class single from Alton to Newcastle (So it could be said that it is one journey with split tickets as I fully allowed to have more than one ticket for a journey). My train from Ropley to my connection point at Alton (with say more than any valid connection time) is delayed as a result of the Mid Hants Railway, such that my SWR train to Waterloo is missed at Alton so I then miss my train at London Kings Cross. Is it then fair that I am unable to claim the delay compensation that I am entitled to for arriving at my destination more than 30 minutes late. I should be entitled to claim from the railway company that caused this delay. Did SWR cause the delay - NO. Did LNER cause the delay - NO. Did the Mid Hants Railway Ltd cause the delay - YES. So who do I claim my delay repay compensation from here? Perhaps if this obligation existed for any operator that enables 'through' journeys onto the national rail network it might focus the minds of the members of staff on these lines to up their game to actually run to the correct timetable. This is said as a volunteer on a number of these operators where the last train of the day has in the past routinely been delayed due to 'awaiting catering staff'.
Putting aside commercial enterprises such as the DSR, do you *really* want to suck money out of a charitable/voluntary/non-commercial/non-profit type organisation in this way (beyond say, a refund if no services run)? As others have pointed out, many heritage railways' finances are *very* tight; this sort of thing would potentially push some over the edge.
If this becomes an issue I would think it would be reasonable for heritage railways to basically say that if you want those sort of terms and conditions, then sorry, don't travel with us, we can't afford the liability (potentially hundreds of pounds for a party).
Heritage railways are struggling heroically to keep ancient machines running on Victorian era infrastructure on a shoestring budget. It's fairly amazing that they run as close to time as often as they do.
Because of this when visiting a heritage railway by National Rail you should either get a ticket which allows flexible return on NR or if you can only afford an advance return, allow (say) a couple of hours leeway during which you can (e.g.) have a pub meal if all goes well, or you won't miss the connection if you're an hour late, or get a taxi to the NR station if the service goes completely tits up.