If I were starting over from scratch .....
I'ld still go with some Harbor Freight items, as there's just no other place around here for me to go (locally) for turning supplies and tools.
I'ld go for either the tabletop or upright version of the full size wood lathe (around 220 dollars), in order to get the power I really want for drilling operations and turning larger items like bowls and vases, which I can't do with my mini wood lathe.
I'ld throw down for a nicer larger belt/disc combo sander with mitre gauge setup to face my blanks ... probably 70 - 80 dollars for the tool, another 20 for the gadget.
I'ld still get the same cheap 20 dollar HFT lathe chisel set, because I know how to grind and sharpen them ...
And next go round, I think I'll just make my own carbide chisel handles and buy the inserts I want in 10-packs. 25 - 30 dollars for 10 ... handles around 15 bucks each.
I'ld also get me a nice 4-jaw chuck .... I'ld love me a Barracuda 2 series ... actually, make that TWO chucks. One for pen blank drilling that I would also use for bowl turning with the wide chuck jaw mount, the other for everyday use. Around 180 dollars each... pen blank drilling jaws are around 30 dollars.
I'ld still want my HFT miter saw, table saw, wet-cutting 7 inch diamond saw ... just for everyday purposes as well as cutting/ripping pen blanks from stock boards (and stone) ...
For dust collection, my vacumn cleaner just won't cut it. I'ld get a real dedicated dust collection system ... probably 2 of the small single-unit type from PSI for around 120 dollars each, and put them on wheeled dollies til I can get a nice large dust collection system to install in the walls of a dedicated wood shop. I'ld pay probably around 500 dollars for the installed version, but I'ld still keep the portable ones on dollies just for dedicated machine use and convenience ...
Now ... if money and shipping were no object .... would I go for the more expensive tools?
Maybe .... but I know right now that I can't afford such things, so I have to stay within my budget. My personal philosophy concerning tools is ....
Use the right tool for the job, even if it's a cheap version, as long as you are not pushing the tool past it's limits it will serve you for a long time. Know those limits and don't try to use a tool for something it was not designed to do.