I just want to say, I didn't intend for THEIR appraisal to serve as YOURS. Just that they may need to have someone (who is not you) tell them what the market is doing, bcs they may be unrealistic about what prices are right now (esp. given that you mentioned "top dollar"). They would probably have to take a loss, and they may not be willing to do that. Since they don't have a real-estate agent, an appraiser might be the "expert on the real estate market" who can tell them. And they might not trust you or your appraiser. And having them hear the bad news about lower prices BEFORE you make an offer might be good. Of course, they might decide not to even set an asking price at all, once they realize the timing is going to cost them $60k. (also, if they do set a price, or you get an appraisal, you might help soften the blow by offering them slightly above the appraisal, if you can swing it)

Here is what I think is going to play out best for you if you are going to be in the house long enough and will heat primarily with wood. Keep in mind that I am an amateur with absolutely no experience in duct systems. I decommissioned mine at the first opportunity and installed mini splits. I'll gladly accept all criticism from anyone that actually knows something. Berto, you've already said that you are going to have ducted AC, (I'd look at mini-split heat pumps, but that is me and I don't have the time to split wood.) It ought to be pretty simple to make a dual furnace system with a wood furnace first in series with the (second) propane or electric furnace. Your thermostat turns on the AHU blower (for me, ideally, a variable speed blower with a proportional thermostat). If the wood boiler is supplying sufficient heat the secondary furnace does not run. If the duct temp between the furnaces falls below a set temp (which might slide depending on outdoor temperature) the secondary furnace fires up. If the day comes that you tire of cutting and splitting wood, you pull out the cheap furnace and put in a mod con furnace. It is no biggie to toss that first furnace because it was inexpensive to start with. The duct system has to be designed to support both heat sources and cooling. The furnace that you choose will have to be just good enough to run a cooling system well which might be more costly than the least expensive that you might use for (back up) heating alone. Keep in mind that a (complicated) super efficient furnace or boiler is not going to be a good investment in a well-insulated and sealed house that is primarily heated with wood. The ROI time will look like infinity.

Cost per square foot for remodeling versus building new is always going to be skewed. Reason? To remodel, the existing structure must be disassembled to a point to rebuild. Double labor. New construction is simply building to finish. Single labor. The tipping factor where remodeling is more expensive than rebuilding varies tremendously. If the building requires plumbing/electrical/HVAC reworking plus structural changes, chances are building new will be less expensive. And may be faster. Minor plumbing/electrical/HVAC/structural is always less expensive. In your case, the tipping factor is how much you intend to do. Straightening walls/floors can be a major overhaul, especially when a complete roof is in the plan. Adding bigger windows is a major remodel, and is more expensive than simply replacing windows. Reason? Sheet rock has to be removed, exterior siding has to be removed past the dimensions of the new windows to allow proper framing of the new openings. New window costs, labor to tear out, and labor/materials to replace sheet rock/siding. If the siding cannot be reused(after being removed) new siding has to be bought/installed/primed/painted. Replacing four windows can easily require residing that entire side of the house. Leveling floors will require tearing out the old, repairing/replacing the joists. Same with the walls. Roof may need complete rebuilt to be right. Rip off all the old roofing/sheathing/rafters and rebuild from the top plate of the walls. Could all that be done without all that tearout? Not if it is done right.`

Your home is very nice but the problem you're having deciding what route to go is that your home is a mishmash of different styles. The roof screams coastal south yet the brick yells colonial. Add the shutters (colonial) and the Roman pillars (colonial) and it amounts to a split personality. The first thing I would suggest is getting rid of the fake shutters. Unless shutters actually have a purpose it's better to ditch them. The columns are a little more problematic because to change them will incur significant costs. I would go with a simple square column for their chameleon-like properties. But make sure the dimensions work in relations to the size of the home. As much as I am an avid gardener I agree that the shrubbery at the house perimeter needs to go. It overwhelms the home and makes it appear much more squat than it actually is. I don't have a problem with the other greenery, though. I have no experience painting brick in such an environment. Bricks helps release humidity in a building. In Canada where I live, painting brick can be problematic. The continual effect of moisture trapped in the brick can deteriorate it over time. While I live in the north I have a place in south Florida. Most painted homes I see are stucco which lends itself to paint. Paint would be an easy and cheaper fix in the short term, but I believe it would require constant attention and over time the costs could multiply. I think your dissatisfaction in your home's appearance is less because of the brickwork but because of the stark contrast of a very light roof against dark facade. Try painting your front door a different color (the red just accentuates the colonial vibe) that works with the brick and the roof before making the leap to painting the whole house. I suggest SW's Sea Serpent. Paint the columns (not the door color) as well but a muted shade like SW's White Flour to get an idea of what your home could look like without going all in on the facade. I noticed you used an app for a combo of house paint and shutter colors complimented with blue and white greenery. As an expert gardener, I have to say my experience with blue and white florals paired with rich dark greenery , which are absolutely sensational, really only work in environments that enjoy a lot of shade. It's the shade aspect of the colorations that makes the pairings so luminous. In a sun drenched environment like south Florida they look washed out. My final suggestion if cost is not an issue would be to hire someone, after investigating the effect of paint on brick, to stucco your home's exterior. No better time after pulling out the foundation plantings.