Reddit mentions of POUND HD Link Cable for Sega Dreamcast

You should search on OfferUp or Facebook marketplace to find the Dreamcast if you can! There is a way to connect a USB keyboard to the Dreamcast, but it's a pain. Everything else is an eBay thing to get!

Also, don't get the VGA to HDMI thing! I would recommend going for this:

https://www.amazon.com/dp/B07BZP7HML/ref=cm_sw_r_cp_api_fXyTBbM941B0C

I use the RetroBit VGA cable and despite needing to kind of force it in the first time, the picture quality is fantastic. I don't have it hooked up to an HDMI converter, though.

You could always just buy a Dreamcast HDMI cable these days.

If you don’t want to use a component cable there’s this

https://www.amazon.com/POUND-HD-Link-Cable-Sega-Dreamcast/dp/B07BZP7HML

Since VGA is Analog and DP is Digital, you usually need a powered adapter. Also, all the adapters I've found have been DP to VGA, not the other way around. When dealing with VGA the direction is important. I think you could possibly do it with a VGA to HDMI adapter.

https://www.amazon.com/VicTsing-Converter-Adapter-Output-Female/dp/B00K4W62R4/

Followed by a HDMI to Displayport cable.

https://www.amazon.com/Rankie-DisplayPort-Cable-Resolution-Ready/dp/B00Z05JMKO/

The best route might be a Dreamcast to HDMI adapter

https://www.amazon.com/HD-Link-Cable-Dreamcast/dp/B07BZP7HML

followed by a female HDMI to Displayport.

https://www.amazon.com/DisplayPort-Adapter-Benfei-Converter-Gold-Plated/dp/B017Q8ZVWK/

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It's certainly possible, but it'll be a bit more work than I think you envisioned.

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Edit - P.S. Be sure that the Displayport on your iMac is a displayport in and not a displayport out.

P.P.S. It seems the Female HDMI to Displayport might be one direction as well, DP-->HDMI

Let the TV do the upscaling. Those TVs do upscaling great and any cable will be far worse at upscaling than the TV. Use the HDMI cable I bought here:

https://www.amazon.com/gp/product/B07BZP7HML/ref=oh_aui_detailpage_o01_s00?ie=UTF8&psc=1

This just arrived yesterday and it works great hooked up to my monitor I usually have my desktop plugged into.

POUND HD Link Cable for Sega Dreamcast https://www.amazon.com/dp/B07BZP7HML/ref=cm_sw_r_cp_apa_i_2wRUCbMC6VTGP

Is this the cable I am looking for?
https://www.amazon.com/HD-Link-Cable-Dreamcast/dp/B07BZP7HML/ref=mp_s_a_1_2?ie=UTF8&qid=1538963231&sr=8-2&pi=AC_SX236_SY340_QL65&keywords=pound+hdmi+cable+dreamcast&dpPl=1&dpID=41s0wczCWGL&ref=plSrch

Does your TV have a hdmi port? You could buy a hdmi dreamcast cord POUND HD Link Cable for Sega Dreamcast https://www.amazon.com/dp/B07BZP7HML/ref=cm_sw_r_cp_apa_i_57xBCbENXH6D7

This might work for you.

So idk if I'm getting this right your trying to use a RF cord to display the dreamcast but since you use RF to get your TV channels it's kinda blocking them if you have both plugged in the same time?? Here in the US there is nothing on channel 3 so when you set the RF cord to channel 3 it will display on that. (I could be talking about something completely so disregard that if that's not what we are talking about lol)

https://www.amazon.com/HD-Link-Cable-Dreamcast-Sega/dp/B07BZP7HML/ref=as_li_ss_tl?ie=UTF8&qid=1528125598&sr=8-1&keywords=pound+dreamcast&dpID=41NTgdULamL&preST=_SY300_QL70_&dpSrc=srch&linkCode=sl1&tag=metaljcom0e-20&linkId=8d1e95cb1487e8913f4ad8d95f4653ba#customerReviews

?