For tent I would go with the Big Agnes Fly Creek UL 2 it is a two person tent that tends to be lighter comparatively to a lot of single person tents and is always well rated and reviewed. Having that extra space without extra weight means more comfort and storage possibilities.

For sleeping bag I like the UltraLamina from Mountain Hardwear (whatever temp rating you might need) because it is a decently light synthetic bag great for all conditions and quite comfortable to sleep in. I have the 45˚ bag and it works for most of what I do.
I would put that bag on top of a Sea To Summit sleeping pad (most of your heat is lost through the ground) which is very comfortable and easy to inflate and deflate. Instead of having long vertical tubes or many horizontal tubes it has smaller individual air pockets which provide a lot more comfort and stability so your pad doesn't fold up on you while sleeping and doesn't transfer motion from cell to cell. They are also quite lightweight and you can get them insulated as well.

I also highly recommend a sleeping bag liner such as the Sea To Summit Coolmax Adaptor. I have two of them one in plain Coolmax and one treated with Insect Shield and it is great either for summer time when it is too hot for a sleeping bag or for keeping the funk out of your sleeping bag and being something easy to wash. It is like a performance sheet sack. STS also makes some that add warmth to your bag if you should need that.

For rain gear I am a big fan of Mountain Hardwear again. Specifically anything with Dry.Q Elite which is a very nice air permeable waterproof membrane. I have the lightweight reasonably stretchy Seraction Pants which were designed for ice climbing which is high output and and the kick patches on the inside ankles are great for cycling to help protect against getting caught by the chain. For jacket I have the Chinley 3L but I don't think they make that anymore but any of their Dry.Q Elite jackets would probably work well. I chose what I chose because of the pockets for non-cycling use.

You could also go with Arc'teryx which makes some awesome jackets with Gore-Tex (and other materials) and either has or soon will be coming out with a jacket or jackets with the new Gore-Tex Active which is supposed to be a lot lighter and more air permeable and keep the water out of the jacket completely rather than having a sandwiched membrane and a DWR coating on the outside which can get soaked through. You can also find that technology from Gore Bike Wear which makes some great cycling specific pieces if that is your thing.

I do recommend doing a shorter local easy tour to test gear and make sure you would be comfortable going further and figure out what you know you need and stuff you might not. Especially make sure you know how to put up your tent in good conditions and use other gear. Learning how to set up your tent in a rainstorm would not be fun.

Things have changed a lot since the 70s so while your coworker sounds awesome and probably still has a few useful tips, you should know the information is quite old and might not still hold up. A lot of technology has improved and become lighter, stronger, faster...