On the ToDO list is write a HOW-TO for the OpenSIMH site... [truth is this has been discussed and explained in earlier messages and Oscar has some info in his manual].
The short form is the easiest /cheapest way to use modern HW is with USB to RS-232C conversion, although if you can get your hands on something like an old Livingston IP-based Ethernet to 8/16 port MUX of the equiv that works fine.
Linux will recognize most of the USB chips, but .... not all of them have all functionality, and there are trade-offs, for instance, some of the FTCI chips support RTS/CTS-based flow control, but will only go down the 30 cps (300 baud). So I recommend that you find out which chip is being used in the system you are getting and download the datasheet. FWIW: The ones based on the Prolific PL2303 can support 10 cps (110 baud for a traditional ASR 33), but I've had problems with flow and buffering on some of those cables. There is a third popular chipset (CM340) that is sometimes used. I have devices with it (Arduinos) and Linux talks to it just fine, but no longer any cables based on it, so I can not give you current experience with SIMH. I also have a 4 port box that works quite well, I've forgotten the Si that its based on - I think it may be a FTCI 4232 but that's by memory.
Simply plug in the cable -- Linux will recognize it - do a: ls -l /dev/*usb* and you should see them.
In simh: type the: show serial command and then "attach DEVXX PATH_reported_by_linux" <-- DL/KL11, DC11 and DZ11 are popular for most PDP-11 OSses
Now your PiDP-8 or PiDP-11 will have that port as whatever type of device you choose to use.
Also, remember that Linux (which SIMH is running) will accept characters from the emulated OS much faster than the original DEC HW - so people have had issues with different target OS - this causes unexpected/surprising behavior - particularly for newbies. Again all this has been discussed before -- Internet search, and the archives are your friend ;-)
Send me e-mail offline if you need help/explanation.
Clem