[Due to the word limit I have had to split this into Part A & Part B]
Contrary to some misconceptions the majority of Tory voters aren't amoral finance types. Many of them are just middle-income social conservatives who though are slightly more cushioned then low-income Labour voters from the social effects of Tory austerity (which they still think is somehow necessary though their attitude on this is beginning to shift if polling is to be believed) are sufficiently socially aware enough of the economic/social consequences of Tory austerity.
In order to reach out to them more effectively & to perhaps some of them into either voting for Labour or not voting Tory (next best thing!) I propose that Labour adopt (from 2020 onwards?) the following approach:
1) Win over current Tory voters in marginal parliamentary constituencies by challenging those Tories (e.g. on social media, doorstep, 'local manifestos', local press) on whether it's (morally?) better for the markets to serve ordinary families rather then the other way around & whether it's truly conservative to have an economic system that can only exists (e.g. 'gig economy' that increases debt & tenancy insecurity) by weakening the financial independence of low income families, as well as middle income families, is a system worth propping up if it leads to the break up of families (e.g. their children being taken to care, one of the partners become so indebted that whole family risked being forced to live in 'insecure' rented accommodation).
2) Challenge Tory voters (i.e. on social media, doorstep, 'local manifestos', local press) in marginal parliamentary constituencies on whether it's truly conservative (i.e. in original sense of the word 'conserve = protect') to propping up an economic system (e.g. not regulating 'Zero-Hours-Contracts' or insecure debt/tenancy/banker profligacy) that makes the family (i.e. the average UK household) such a socially unstable institution (e.g. main bread winner risks losing their home & means of providing for their family) that it's one financial crisis away from becoming homeless & their children being taken into care or their children becoming part of a 'lost generation' that can never start a family of their own because they will never be able to afford a house but are always (i.e. that generation) moving from one insecure tenancy to another whilst working in multiple Zero-Hours-Contract jobs with no roots anywhere.
3) Challenge Tory voters (i.e. on social media, doorstep, 'local manifestos', local press) in marginal parliamentary constituencies whether they think it's truly conservative to maintain an economic system (via austerity) that makes their community physically unsafe (e.g. fewer police officers to patrol their neighbourhoods, more violent criminals given probation by a Tory-run Ministry of Justice due to the penny pinching of Chris Grayling, OAPs dying in home due to local government social care cuts, fracking poisoning their air & ruining the beauty of their surroundings).
4) Challenge Tory voters (i.e. on social media, doorstep, 'local manifestos', local press) in marginal parliamentary constituencies whether they can be certain that they themselves are less likely to lose their jobs or savings if the current economic policies of this Tory government (if it continues for another 5 more years?) triggers a recession (with it's subsequent cuts to social care & NHS?) rather then what ever uncertainty they imagine the policies of a radical Labour government may bring.
[See part B - final part]