Bryan, if the driveway needs to be removed and re-done, you could probably easily spend a large part, in not the bulk of your budget ($10K that you don't want to spend) on that single project and its accessory parts, depending on what you do and how you do it.

Like every other service from heart transplants to getting your shoes polished, you either need to know (or learn) how to do it yourself or hire someone who knows how. It's no different with landscape design. (Design is the "thinking through" portion of landscape work that determines what the actual physical work of the project will be. It's an important part because it determines if each dollar spent is worth a dollar, or if it's only worth 25 cents ... or even less ... meaning, will you or someone else actually like and want what is produced? Or will there be ongoing complaints about how it really doesn't work or look good and when it's time to sell to someone else, all they'll think about is how it needs to be ripped out and de-done?) There are landscape designers everywhere. If you don't think you have the talent (or will, and time, to learn and do) then interview some landscape designers and get an idea of how they could help you and how much it would cost. Some $ spent on the "thinking through" portion of landscape work can prevent much wasted $ on the actual work itself.

Transforming a garage into living space does create the age old dilemma of the existing driveway suddenly going nowhere. That, however, may come in handy in the short haul when doing future renovations. The siding doesn't bother me since it's a common occurrence for additions to have a different treatment - cost, can't match materials, you name it.

What does give me pause, though, is the 3-stall carport. Might be sturdy as Gibraltar, but it has a ramshackle appearance and is the greatest detractor from your home.

Enclosing the carport and creating a bona fide garage would get my attention first. Then I would consider a new driveway in the "right" location and demolishing the old. Then you can go on to the landscaping and finishing touches, like cobblestone pathways, etc.

Overall planning certainly doesn't hurt, even if some things are way down the road.