Those look like 20" rubber not the 15 that most lowboy's from that era had. 9.00x 20, You can mount tubeless demountables on there 295-75-22.5 would be the same OD or you could go smaller 255's which would lower the deck height a bit.
I think I'd start by assessing what is there, and how well it is done.
If the axles are installed in alignment with the king pin, I wouldn't change. If it was scabbed in and everything is out of alignment, then you are going to have to cut it out to align anyway. Alignment is done by how the brackets are welded on. Everything will be "floppy" until welded, and you better get it right.
One looks to be "Propar" axle and one looks to be a axle where the spindle is smaller for the outer bearing.
One thing I see in the latest picture that concerns me: Will the tires clear when the suspension is tilted to either extreme?
It looks like they will hit when the rear is compressed fully and the front might hit when it is compressed fully.
Better to find that out now, rather then after you do all the work. It wouldn't surprise me to learn it had 15" hubs on it from the get go, and someone changed without checking clearances.
New axles with 12" brakes and 17.5 tires would be the modern equivalent. I did one axle job on a trailer, measure 4-5 times and weld once!