There is a lot involved, and some of that is luck. It also takes research, perseverance, training the eye, knowing when to look, and where to look.
Research---- They had to have water, they camped where there was a steady water supply. Every state has what is called "one call" system. As in Missouri One Call, Florida one call and so on. One call is a system where contractors can call in to request a utility locates. Each One Call center has maps that they will give out, these maps list rivers as well as small streams, creeks, natural springs. They list county roads, and dirt roads. They also break the area down into range section, quarter section. Do a search for _ _ _ _ _ one call in google, call them and tell them you are trying to get "one call" maps for locating..
Protection from the cold, I looked for bluffs that were at least on the North or west side, constant water close by, and if there is natural woods there, chances are good its been there for thousands of years.
Make friends with and talk to farmers. I have gone up to them talked to them, been friendly, then asked for their permission to hunt their fields. I stressed I would not damage an crops, I would not be digging, only surface hunting. I usually got permission to hunt the fields, especially where they turned it over and had not planted yet. Many times I carried extra cokes and pepsis, and bottles of water in my truck, offering them something cold......I averaged probably 3 yes I can hunt to every no.
Perseverance---Keep looking, you will find them if you look.
Train the Eye---Lots of new hunters look for points laying on the ground, ,most of the time when I was hunting I would only see a tip, cornor, edge on a point. I started hunting fields, then had someone teach me how to hunt creeks and streams. I preferred the water hunting, I found a lot more whole nice points there.
Look down stream, in stone or hard bottom creaks and streams, especially after a hard rain. Look anywhere where something can drop and be out of the flow of the current. Look behind rocks, fallen limbs, brush and trash. Wide creeks are usually better, and deep sides even better. That usually means they are old. Natives camped along side of them, as the sides cave in from erosion artifacts fall in them, and are washed down stream in heavy rains. If you can find small water falls, where they drop a foot or two, there will be a hole the falling water makes, dig down there, I have found many there when I lived in Missouri.
Look for plowed fields, then when you get a rain, especially a heavy rain go back to the fields, any points will be shiny from the water and many times they stand out, sitting on top of little mounds where they protected the dirt under them. Many times I would be out in the fields in the rain, wearing mud boots looking for points when i lived in Missouri.
When to look----Any time looking beats not looking, but like I said, looking after rain storms, fields or creeks and streams is one of the best times.
Good luck and remember A bad day hunting beats a good day at work.......