Does the Transport make a significant difference

Hard drive is better...imo. transports not as much as other components. And....in most cases, very little. To compare a transport to a tt, arm and cartridge is a far reach. Money would be better spent on other components or software.

I just had John Tucker upgrade my Oppo 105 and it is outstanding. One player that does it all. I owned the Ayon CD-5 and the PS Audio PWD MKII and they are not even close to as good as the T105. Something to consider.

I sold my Parasound P5 and ordered a PS Audio PWT. My next step will be a preamp.

DACs with analog volume control and tube output stages might be better positioned to go direct into amp. I'm thinking products such as Aesthetix and EAR etal.

What Sonic difference are you looking to obtain? That would go a long way with recommendations. BTW, you might consider measuring your rooms response and room treatments before spending any more money. That room looks pretty empty and reflective.