Wellspring, thank you so much for your response. I really appreciate you taking the time to read my post and your concern regarding drainage, which I'm afraid I made sound like more of an issue than it actually is. We too were initially concerned and had several experts (an engineer, a home inspector, a survey team, and 3 contractors) examine the entire property prior to our purchase. They all agreed the small amount of run off we see after heavy rains is not in fact getting near the foundation or the house but rather staying about 2 feet away due to the grade of the ground right up against the house. I should have used better wording in my original post and for that I apologize. Another contributing factor to the run off is the condition of the ground. The front oak trees were so overgrown for so many years there were literally branches touching the ground and consequently no grass and hardly any ground cover at all growing in the front yard. As a result, the ground itself was very compact and much of the top soil had washed away. We wanted to wait until after we finished the construction on the house to start working on the yard so we are just now beginning to address the issue. From what we have been told, proper aeration along with the addition of top soil and organic matter, as well as some actual grass, should really help with the small amount of run off. As far as gardening and yard care are concerned, I am just an enthusiastic novice so I tend to believe what I am told. If this does not sound plausible to you, by all means, please let me know! Thanks again and any landscaping ideas are still welcomed.

The first question..."has the tree outlived its usefulness?" begs another, HOW is the tree useful? Like a giant parasol, it provides protection from strong summer sun. It even provides a little protection from beginning rains. Visually, it adds interest as a sculptural object. And it frames and enhances (or obliterates depending on how it's controlled) the view of the house/property. I cannot see that it has outlived these functions. But I can see that it could be controlled a little differently so it does a better job of framing the view. Here's a little sketch that illustrates my point. I offer it not to convince you, but in order to let you know what to look for as you observe trees in others' front yards. As you travel about during the day, notice the difference in effect between trees that have been limbed up and those with low-hanging limbs. In general, large older trees that are limbed up present a cleaner, more stately appearance. If they have been limbed up properly (with balance and without protruding stubs) the character of the trunk may be much more impressive than one which has the competition of low limbs and foliage. The tree on the left competes and obstructs; the one on the right frames and shelters. Take this suggestion with a grain of salt as it's based solely on the view shown in the next photo. I've marked red Xs to show which limbs I'd probably remove, but this is something that would really depend on what the tree looks like from all angles of view. The goal would be to have the tree be balanced from all views and get the limbs high enough to visually clear the house. Remember that limbs left on the tree will get LOWER in the future as they grow longer and heavier. (It is hardly ideal to "organize" the branching structure of a tree after trees have grown for many years without guidance. It's far preferable to prune frequently along the way. But we're working with what we have.) Keep in mind that limbing up the tree also has the benefit of allowing more light to enter below while still retaining the tree's ability to shade from the high sun. This means that one's ability to grow other landscape plants below it is improved. "Is the tree too big for the house?" Imagine a little log cabin at the base of giant redwoods. Could there not be a more charming picture? In my view there's no problem whatsoever with a tree towering over a house. But they need to work together, not be in competition. The tree should shelter the house, not obliterate it visually. The tree roots should not interfere with the house foundation. One must desire the shade. When those requirements are met, a tree can be welcome. Though big old trees sometimes do fall over in severe storms, the likelihood of this happening is small enough that one can find thousands of danger-causing conditions that can be worried about before it. I just measured the trunk diameter of an oak tree that stands 14' from my house. It's 62". But before I would cut it down (It's benefits to me are tremendous even though it can also be a PITA,) I'd quit driving or riding with others as that's far more dangerous and likely to cause me injury. Keep the new walkway WELL clear of the tree trunk. I think you must pay much more attention to the geometry (shape and layout) of the new path than what is shown in either of the proposed schemes. It is a built object that is an extension of the architecture. It should demonstrate this. Because of the tree, it would almost certainly have a curving component to it. You might need professional assistance here to come up with the right scheme. (Though it MIGHT work out that way, in my mind, it is not a "given" that best location for the porch steps is at the center of the porch. Design is often a balancing act and you'd be considering more than just the porch and the steps.) Regarding "what to plant in front of the house"...the first thing to do here is work out the shape & form of the plant masses before thinking about the species of anything. You have to do this before you can figure out what plants are capable of making these forms. Consider that a very attractive custom built section of decorative fence could be the basis of screening the AC unit. It could be an opportunity to further enhance the architecture of the house and work in unison with plants. For some brainstorming ideas, Google images for: air conditioner screen.

Front yard patio, perhaps encircled by low shrubs for a bit of privacy, with grass between that and sidewalk. https://www.houselogic.com/photos/yard-patio/front-yard-patio-ideas/slide/patio-as-focal-point/ If liriope will live in your planting zone, consider outlining your sidewalk and driveway with that … or something similar.

As I thought there are a lot of different views on trees from everyone. Personally, I'm not concerned about removal pushing buyers away if I ever sell. This home sits on a large natural lake. So there is plenty of appeal here. I think its really going to come down to my personal preference on how I want to live with this tree and its maintenance. The shade factor is really the only thing I enjoy about it (which of courses is huge in Florida). Leaf fall, pollen and sidewalk damage are the frustrating parts. I appreciate everyone taking the time to provide their thoughts on this. It is differently helpful as I make my decisions. The graphic Yardvaark provided was also helpful. Whether I leave the tree or not, I'll be looking to fix my walkway and I like the curved design you suggested.