Doug,
Your retirement idea is indeed a good one, BUT...
You will get more income and more profit if you do kiln dry the upper grades.
You will find that oftentimes and maybe always, you will spend more time marketing and selling than sawing and drying. In fact, you can saw all day, every day of the week, but you only make money when the lumber is sold.
In your business, there will be times when you need cash (sales are slow; a good deal for some logs comes up; maintenance, etc.). So, always keep as much cash as possible and buy equipment using credit or a loan from the bank. Small business groups in the state may be able to help identify good sources of money; local banks are often excellent too.
Get a business plan that identifies who you are, what you can and will do, what you will not do, markets, and so on. Again, state small business people (often through the county extension agent) can help.
For equipment, buy equipment that someone else has already done all the research and testing. In other words, buy top name brands. Buy "Made in USA" for good maintenance. (For sawmills, choose a big company and the size mill that they sell which will work for you. Then use that piece of equipment to compare to everyone else's equipment. Use a similar approach for a kiln.) Visit someone nearby that has the same equipment and see it running.
Although the upper grades often can be sold easily and with reasonable profit, the lower grades (sometimes 40% of a log is low grade lumber, or more) must also be sold. Profit is less with lower grades, so do not spend lots of time with them in manufacturing or marketing. A business plan forces you to consider all these aspects in advance.
Consider purchasing a kiln first and having all the logs sawn by a contract sawmiller for you. This costs a little bit for sawing, but does mean that you do not have a capital investment and sawmill maintenance...or the mess of a sawmill - - bark, slabs and sawdust. Plus, with a kiln your labor will be less so you can go fishing during the day and then check the kiln at night.
With a kiln, check out a DH kiln that is in a well insulated reefer van. Lots of postings about that here, plus I believe NYLE has some plans (and they credit what the plans cost against any purchase you make). Again, I like something that I know will work, rather than something that I have to do some testing or engineering because the company has this new product, etc.
If you do put in a permanent kiln building, always think ahead and make sure its location is perfect; that is, should you double your size, check that the first kiln is not in the wrong place when you expand.
Contact your power company's business office and they can help you with the best rate for a kiln (which is running 24/7, which means low peak demand). I have heard that because a DH uses a heart pump, that there were some special incentives for that in at least one state.
Finally, join a drying association. Many meet several times a year and have both plant visits and technical presentations. Most have beginners classes too. There are active kiln groups in the Great Lakes, Ohio Valley, PA, New England, Southeast (VA, NC, SC, GA). Of course, you could hire me to come in for a day or two, but that is expensive...the best is always more expensive (LOL).
Attend a 3-day hardwood lumber grading class and also a 3-day drying class. You will also find that within our industry, your competitors are often very willing to share with you.
Questions?