This is a very big and nuanced subject, and I think it oversimplifies the issues too much to choose which of liberals and conservatives better represent Jesus. There are certainly aspects in particular flavors of each which one would better associate with Jesus. However, in general, on the high profile moral issues and general approaches (as compared to each of their perhaps well-intended ends), most of today’s liberals fail the test big time. If the question is regarding government assistance programs, taxation, etc., then the conservative also tends to align more closely. Liberals talk a good game about helping others, but they want to do it with other people’s money, and they want to do it through institutions and programs, neither of which I believe Jesus would condone. The conservative cause has largely lost this as a talking point, but it’s unfair to suggest they don’t want to help others, it’s just that they don’t think it is government’s role to do so and that more people can be helped better through other means (to which predominantly I think Jesus would agree). First, we need to distinguish between mercantilism/corporatism and broader conservatism – the former Jesus would have little interest in, the latter more so. The problem is, the lines are not very clear, so I have to distance somewhat from that aspect of many conservative positions today.
In general, Jesus was anti-establishment/anti-institutionalization. He was not against money, or even wealth. He was certainly not an ascetic, and I believe most of the statements about money have been misconstrued. He wasn’t necessarily suggesting that the rich young ruler, for example, should have no money; but, he was very concerned with the ruler’s attitude about that money, and that this heart-defect prevented him from following Jesus. He also did not require that the apostles give up all they had, just that they needed to be willing if called to do so because to follow Jesus was to sell yourself out as slaves and stewards (to him, not to the state). All they had was now in trust for his purposes, including time, money, possessions, passions. His disciples may have left their boats, but they weren’t required to give them away – they actually continued to use them throughout their ministries, as they were doing with their homes, etc. The problem with the rich young ruler was not that he had wealth, but that he valued it more than serving Jesus. Jesus doesn’t require 100% of what we have to be given to feed the poor, but he does require that we recognize that 100% of it is available to do whatever his spirit leads us to do with it in furtherance of the kingdom of God. That may lead one to start a non-profit and take no salary; that may lead another to keep wads of cash for handing out; it may lead another to save wisely and start a business that employs others or develops a product or a process that cures cancer or increases crop production or eliminates mosquitoes and malaria. It may require that one not squander on consumer items and save to support parents or other family members. Most definitely, there was no anti-investment mentality. The stewardship principle taught by Jesus was to use all the gifts we’ve been given to their best use, including investment. Just as a trustee would be fired for failing to grow its ward’s funds, we are to build on and increase what we have to share – true enough, too many fail to think of that growth as being for the benefit of Jesus and his mission and for others in his name.
All of that, though, is individual and relational and is entirely consistent with Jesus’ teaching as well as that of the underlying conservative message. Individual “liberty,” itself, is largely a Christian ideal – it’s ironic because Christianity at its core is about servitude (to Christ). The difference is that Jesus taught you can’t serve two masters, that enslavement to a state (whether actually or practically speaking) or statist system or any other institution works against the system of Christ. Whether we’re talking about Atlantic slavery, slavery to one’s desires, slavery to an employer, to a creditor, or an addiction (or whatever), all detract from our servitude to Christ. That is what salvation is about – we are saved from ourselves, from each other to do his will here and now and to reflect or embody the nature and character of God. There is a future hope and that is very important to the Christian, but it’s not principally what Christianity is all about. It is too often the focus in today’s churches, but today’s churches are full of professing Christians who Jesus may well not consider as his disciples.
Further on “investment,” Joseph was actually commended for “hoarding” but it wasn’t hoarding for his own (or even his boss’s) benefit. It was good stewardship which benefitted others. Importantly, he didn’t confiscate the wealth of others, but bought up their crops to build up a storehouse which ended up bettering society at large, whether they realized it or not. If he had merely shared the king’s (or others’) wealth with those as needs came, they would all have starved - - that is a VERY conservative message and anti-“liberal” one.
I don’t believe Jesus would be too keen on the dogmatic self-reliance and self-determinism that many conservatives today embody, and voluntary communal concepts (without the morality issues in the liberal flavors) probably would be more Christ-like but for the more likely communism statist systems that tend to emerge from those ideas.
It's important to understand that Jesus was not, principally, a moral teacher. He was not just a guru leading people into enlightenment about helping others etc. Principally, he came as crown prince, and he and his apostles spread the proclamation of his lordship and his rule in the kingdom of God. He was in many ways a radical, against the establishment and as part of the proclamation that he was to be and had become king was the declaration that Caesar and all such regimes were not. This, and a familiarity with the Caesar cults that surrounded the coinage issue help to understand the VERY clever “render unto Caesar” response. There is a lot of context and subtext to this, and though there are a lot of various interpretations of this, the following site reflects much of the history and background and is pretty close to my own views on the exchange. http://www.lewrockwell.com/orig11/barr-j1.1.1.html
The kingdom of God is a spiritual Kingdom, and virtually all of Jesus’ ministry was directed to proof that he was who he claimed to be, and also to illustrate aspects of this kingdom. Many of the illustrations drawn about money and other things are lost to the obvious while failing to realize the spiritual lessons being illustrated. This is another area where many conservatives probably don’t reflect the Christian message – for a Christian, the emphasis on nationalism is a bit inconsistent as we may live in a nation and be subject to its laws and rules and be required to follow them (so as not to be a reproach to Christ) but scripture tells us our “citizenship” is of this heavenly kingdom and that we are subjects of another king and are as ambassadors living in another land. We are to respect the nation’s laws, etc. but with our allegiance first and foremost to our true king just as clearly as if it were an earthly kingdom. Should we engage and try and influence change that would be just and righteous and increase liberty and encourage people to work and not to be a drain on society? Yes, those principles are definitely scriptural. But, I do agree that the emphasis many Christian conservatives place on politics and social policy tends to rely more on the state and less on Christ to solve our problems. So, Jesus probably was more of a libertarian than a modern conservative, but many of the principles are quite similar.
As an aside, I believe he would be just as against the institutionalization and corporatization of the church as he would the state. The kingdom of God is present “among” the people, each acting individually and as the spirit guides them. Institutions crush this, and the further you remove individuals from the equation, you move further from the work of the spirit and the justice and mercy that he intends us to reflect. Institutions can appear to be efficient in some respects, but in the end it is only individuals who can determine whether a handout, for example, would be loving for another or enabling to their destruction. Institutions aren’t good at that. That is very much a conservative message, and is key to the teachings of Christ and the whole system of the kingdom of God. In my view, much of the apocryphal imagery in the Revelation is directed at social and religious “institutions” and corporatist or totalitarian control of each (such as was embodied by the Caesar, the Roman institutions and the arising “Roman” church structure/institution/”leadership”).
You didn’t raise it, but the issue of “war” raises especially tricky questions – generally, Jesus taught pacifism, but only as it pertains to self-defense. Protecting others, helping the oppressed, etc. may well require war even violence and especially self-sacrifice. Defending a neighbor or family member may require me to shoot a man. Defending myself not so much. Beyond that, it’s very tricky to determine when it is more loving to act than to sit it out.