Chippy, In general, agriculture is not much of a paying proposition on a small scale. Few people actually make a positive cash flow on small acreages unless they develop a niche where they have a competitive advantage.
Most of what I see in smaller operations, especially in cattle, is retirement checks subsidizing what are actually hobby farms or ego farms (I'm a cattleman!) There are a lot of folks with a 9-5 gig in town to have the money to support their illusion of being farmers or ranchers. In many instances a good hard nosed appraisal of the "buisness" would detect undeclared bankruptcy.
A lot of folks here about "run a few head of cattle", it is a respectable thing to do, gives them a sense of membership in a way of life but rarely makes much profit. More often than not refusal to adhere to best modern practices reduces or elliminates actual profit. For example, if your "calf check" goes to the feed store to pay for feed and supplies what did your effort and time buy you besides a dangersous expensive hobby?
With your motivation and past record of working long hours, perhaps you should consider what skills you have that are marketable. Fewer and fewer people are willing to show up on time clean and sober and actually perform. Every sub contractor I have talked to all had the same complaint... finding honest help that new how to do anything and would reliably show up and do it.
If you are set on agriculture, either find something that others are sucessful at that you can emulate or find a niche where you have a comparitive advantage or at least a favorable economic climate.
Not to be too negative or discouraging about brush hogging or otherwise working your tractor or growing tomatos or whatever but there are just a lot of folks moving out of the "burbs" to the country who want to find something to do part or even full time to make some money and or defray the costs of the newfound toy universe (ag machines). Many of these set low prices to ensure getting work but are not realistic, often not including amortization of equipment, money set aside for repairs and replacements of capital equipment. They buy a tractor and some equipment and will work for little more than the cost of fuel and lunch just to be able to get paid to do something they think of as fun. Good for them, BAD FOR YOU. There are always folks buying some dirt equipment of some sort who think they can pay for it by working some part time jobs and maybe make a couple bucks. In general they do not last but there is a constant stream of them. To what effect? It keeps someone with realistic prices that are fair and might keep them in buisness from being able to compete in a fair segment of the market. The guys who are doing it as a hobby (whether or not admitted) actually ruin the market for professionals in some endeavors.
Hopefully you will choose wisely and not burn your nest egg in some thin margin enterprise that any Johny come lately with a tractor could replicate if he didn't mind having to subsidise the "project", just to get started you know.
* You Can Farm: The Entrepreneur's Guide to Start & Succeed in a Farming Enterprise by Joel Salatin (Introduction), Allan Nation (Paperback)
* Small-Scale Livestock Farming: A Grass-Based Approach for Health, Sustainability, and Profit by Carol Ekarius (Paperback)
* Making Your Small Farm Profitable by Ron Macher, Howard W., Jr. Kerr (Paperback)
* Storey's Basic Country Skills: A Practical Guide to Self-Reliance by M. John Storey, et al (Paperback)
* Successful Small-Scale Farming: An Organic Approach by Karl Schwenke, Ben Watson (Editor) (Paperback)
Pat