I am of the front end school. But for what it is worth here are my suggestions.
1)buy good used gear on audiogon.
2)Buy the speakers last. Buy good compact 2-way monitors e.g. pro-ac tablette, totem model 1 signature, etc.
3)Buy a good amplifer, preferably 100-150 watts. (musical fidelity, quad 909, ayre v3x, bat vk200, etc.
4) pre-amp is more important than many think. Buy something simple. (pass x2, musical fidelity, etc.)
5)Digital source: something competent (one box player) e.g.
Creek cd50 classic.
6) cables: sensible well made stuff: cardas neutral reference, Goertz alpha-core sapphire for interconnect. non-bi-wire speaker calbles (cardas, supra, etc.)
You should wind up with a very musical and enjoyable system.
The upgrades will be genetically inevitable. Often the first or earliest systems are played in rooms with modest dimensions and small monitors are suitable. Transport costs are less and resale is easier.
Good luck with your decisions!
Appassionata