For starters, you would start off by getting a lumber industry to create a clearing for your stronghold and to provide necessary lumber resources to help reinforce your outer walls, to build wooden watchtowers, and wooden furniture. Next, you would have to establish the closest mine to the clearing of your stronghold and start looking for miners to mine stone for your strongholds outer walls and inner structures. After that, your stronghold will need militia and mercs so next quest tells you to go to the companions or thieves guild to hire mercenary's/thugs to help guard your stronghold. For militia, you would have to look for a ex-blacksmith and pay for a blacksmith workshop to create weapons for your townspeople and to sell weapons for your earliest convenience. Then, your stronghold will need to establish trade with other cities so you would have to pay for a trade shop and commute a worthy economy income for you and your workers at your stronghold. After that, its just the process of building up your mansion in the heart of your beloved stronghold with all the resources you acquired. Visit the trade shop for furnishes and then you have your stronghold!
You have a working mill, several worker houses, a stone mine, blacksmith, bodyguards, a trade shop, and most of all...your precious mansion!! Also you would have a decent population with plenty of action going on so hardly any room for boredom in your stronghold. I think this would be a most fabulous idea to implement in Skyrim for those who want a stronghold in the game. What do you guys think?

You've got it all laid out in great detail. Glad to see that other people really want this too.