I was very much like every man when I started a couple of years ago. I came from years of using an electric shaver. This is actually a little different than if you were using cartridge razors because your skin isn't as accustomed to the blades (in my experience anyway). You can check out full the best budget electric shaver to fully appreciate the prestige of these premium shavers.
Therefore, I would highly recommend a mild razor because of this. There are so many to choose from it's hard to narrow it down to just a couple, but I'll give you some suggestions from my experience.
For vintage, it's hard to beat a 40's SS or Blue Tip. They shave great and are mild enough that it won't be such a shock to your face. I would also include a Slim adjustable or any of the Black Beauties. You can start with them being very mild, and adjust to more aggressive as you get more comfortable. Also, the Gillette Techs provide a smooth, gentle shave as well.
For modern products, the standard recommendation is the EJ DE89 or Merkur 34C. But I would also throw an Italian Barber Teck II. My experience is limited with modern razors, but I can vouch for these.
I hope you enjoy your experience, regardless of which route you take. I'm sure many others will chime in and give their recommendation too. There are a lot of knowledgeable people here who are willing to help.