My first job out of college with a major greeting card company (seems like 200 years ago) required me to spend about 25% of my time shooting photos in all kinds of outdoor locations, all available light, mostly at sunset, trying to capture couples together (I was allowed to pay $10 to anyone willing to model) for romantic images to be used on cards. I was a novice, but since we were doing a lot of experimental stuff and constantly trying new techniques, both in-camera and in the darkroom, failures were expected and acceptable. Spent a lot of time running up and down beaches with two 35mm cameras and one heavy 6x6 bouncing off my chest trying to capture the setting sun. So yeah, I got paid for that as part of my job.
For the last 30 years, I've run my own one-man advertising agency, which required me to be a jack of all trades. I did quite a bit of tabletop product photography for clients, a bit of location stuff, nothing too terribly complex (like Dirty Harry said, a man's got to know his limitations), but I was able to bill for my time and it provided a good supplement to the other advertising services I offered. Also allowed me to write off any camera equipment I bought, which saved thousands of $ over the years. I've also sold a few images for publication, nothing too dramatic.
But, I started with photography as a hobby, and it continues as such to this day. My commercial work helped pay some of the bills, and allowed me to acquire some decent equipment and learn while I worked. It subsidized my love of photography as an art form, and I was lucky to be able to do that.
I think most members of this forum will agree that making money in photography is a daunting challenge, unless you have the desire, the talent, the commitment, and the ability to make the investment required to become a true working professional. Allow me to offer one bit of advice: if you find yourself in the position to actually sell some work, or take on a commission of some sort, do not sell yourself short. Charge a fair but decent price. Do not give away your work or your talents. Most of us in "creative" fields are guilty of grossly undercharging, simply because we are so thrilled that someone would actually pay for us to do something we love. Kind of like getting paid to eat. I have been guilty of that my entire career, and would be a much wealthier man today if I had had the wisdom and the courage to charge what a job was really worth. Took me a lot of years to get to that point, and I still struggle with it. Artistic talent is a rare and precious commodity, something few of us are blessed with, and it should be valued and paid for accordingly.
I will second the recommendations of the members suggesting buying high quality used equipment. I have bought and sold several items through KEH, and been thoroughly pleased. Their grading system is, if anything, on the conservative side. You will not get top equipment at half price, but you can save several hundred dollars over retail. Last fall I purchased a Nikkor 20mm f1.4 specifically for a trip to Iceland to photograph the Northern Lights. Their "like new" lens appeared to me, upon receiving it, to be absolutely new. Saved me well over $100. It performed superbly. It is far better to buy the highest quality slightly used equipment you can afford--if it is in top conditiion--than to buy a brand new item of lesser quality.
I've also had good luck with B&H. Can't comment on the other firms.
Last but not least, do not fall into the trap of thinking everything that is "new and improved" is in fact new or improved. I can verify from all my years in the advertising business that manufacturers in almost every industry are under immense competitive pressures to introduce something "new" every year. I had to help my clients perform this dance every buying season as the trade shows and conventions approached. It is simply not possible, and it is quite rare, that truly groundbreaking improvements can be offered up every single calendar year--especially in relatively mature industries. Don't fall for the marketing and advertising gimmicks and think you always have to have the latest and greatest. Believe me, I know, because my job was to devise those gimmicks, and I was very good at it. Thinking you need the absolute newest of everything will not improve your ability to see, allow you to master your equipment, or to conceive a great photograph. It will merely keep you in debt and trying to figure out how the heck this new gadget works.
Good luck!