Hi Jim. I haven't bought more land, but have had some success with my property in the last two years. Let's see - what have I learned. White clover comes up well hand-sown in poor, acidic clay soils. Black Locust also grows into any soil (currently experimenting with growing even more by seeds). Stumps last forever. I have not ground down any, just using logs to build out terraces between the stumps, and then mowing this to help grass and clover develop. Rye grass, hand sown has done well. Scattered some lime, but it has probably not done much; my ground is so steep and rugged that I broke a spreader. Have gone over some sections with a power aerator and rear tine tiller, but not sure how much they have helped, given the difficulty of working ground. My stumps have grown some nice fungus (have not had time/money to do mushroom growing, but was fortunate enough to have Lion's Mane volunteer on some of my logs).
Shade is my problem, in terms of getting grass to grow in certain areas that are more fern or vine dominated currently.
Have also done well planting daffodil bulbs in forest. Currently planting a lot of Japanese Arrow bamboo to hopefully grow a shade-tolerant hedge.
I've talked to folks at Living Energy Farm that got clear-cut former-land land (presumably for a really good price) and in only about a decade have crops, buildings, fruit trees, etc going. I'm not sure what methods they used.
In terms of location I'm still looking into the Madison/Gordonsville area, but am also looking into Louisa and south of Charlottesville. I'm prioritizing flatness over price/acre and budgeting down a bit too, in terms of building a house for a reasonable price (looking into archedcabins.com). I think 5-10 acres will do what I need, which is have complete privacy, host events of up to 50 people, and support 2-10 people perpetually.
TL;DR - I think my basic idea is sound, but will be moderated somewhat to be a bit more practical.