Looking for advice on setting up a permaculture style lot for lumber and other usable wood

I don't exactly have super specific questions as I'm not entirely certain what to ask.

So I have more land than I can reasonably maintain.  What I'm hoping to do is set aside part of the land for occasional clearing.  But I'd like to set it up in a permaculture style so it can be utilized in between cuts.  I also want to try daisugi methods w/ some pine and cedar.  That said I spoke w/ some local mills and they said it's either not really worth it or shoot for Canary Island Date Palms and Black Walnut.    I'm hoping I or maybe my kids can make some decent cash in 25-30 years.  

I live in FL zone 9, in an area that despite a lot of rain is farily dry.  Everything around here is sand pine all in rows and nothing really interplanted.  I've always wanted to try to see if it could be planted on contour w/ nitrogen fixers in between, blueberries, and daisugi,  etc, etc. so that even it being for lumber the landscape thrives and it's maximized.  I've often wondered if you could get more bang for the buck that way, despite the clearing hassles, larger spacing, etc.  

So for black Walnut I looked up companions and found black locust and red Cedar (I would try to daisugi).  I intend to build them on contour swales and add some pawpaws/mulberries nearby.  Is this even a good idea?  the mills told me they do Cypress (not enough water for that) and the Cedar in FL is constantly hollow.  My hope would be w/ some companion planting the Cedar would grow much better.

The guy from the mill however said natives don't bring any money.  He planted 34 acres of oak and pine and made less than his bud who planted 5 acres of Canary Island Date Palms.  So my next question is, what do I need to grow/harvest those?  I assume they need to be dug up for landscaping and the money part is not in any lumber use.  not really sure how to plant/prep for such a thing.  I need a way to set it and forget it to some extent and don't know if the palms could do that.

Bob said,But I'd like to set it up in a permaculture style so it can be utilized in between cuts.

By permaculture style do you mean growing plants the permaculture way or building soil the permaculture way?

Some say that permaculture is land management.  Looking at this approach then maybe building soil health by adding wood chips, compost and mushrooms?

Hi Bob. It's a bit difficult to give advice on a specific property, especially when it comes to long-term economic choices.

I'm guessing you've been there a while, walking the land in all seasons? That's important in my experience.

I know that the right time to plant a tree is 20 years ago.

I also know it's easy to be overwhelmed with a property that has endless possibilities.

Guess that doesn't solve your problem. But for what it's worth, someone is listening.