Ah yes, the 90s. That explains the mismatched arched window. And the 90s are back. What is not back is inconsistent architectural detailing, so find some examples of houses that look like the overall style of yours and see how the frieze boards and colour distribution have been handled for guidance. If you are having other work done on the exterior and that work is to fix some questionable quality of work, by all means, hire a company who not only knows how to install siding but has a good idea of how to handle anomalies created by additions that don't quite match the original architectural style.

Nice house with great potential. Great yard. You have horizontal siding beneath the exterior equivalent of a chair rail and again in the gable. You could use more of the same horizontal siding all around the house to cover what appears to have been an attempt at a modern stucco look. If you're replacing the siding, you will need to choose siding that stands up well to all weather in no small part because you have almost no roof overhang -- no gutter and no soffit. It might be possible to add that. See diagram in the upper right corner of this page: https://www.google.com/search?q=box+gutter+added+to+end+of+roof&client=firefox-b-1-d&source=lnms&tbm=isch&sa=X&ved=2ahUKEwj6_s-RpbfpAhWJgnIEHQoLARgQ_AUoAXoECAwQAw&biw=1324&bih=648#imgrc=N13gIloutCg4eM If left as is, during heavy rains you should not be surprised if rainwater runs down the side of your home, eventually causing damage. The chimney is not an eyesore but it would definitely look a whole lot better if you could pressure wash or sand blast off or chemically remove the white product --whitewash or paint, etc., -- that someone added over the brick. The greenish gray color of your siding is likely may not be the best choice for your siding but until you get that white smear off your chimney, wait about painting the siding -- unless you intend to paint it all white. If you change out any windows, do that before any changes to the siding -- and choose windows that open/close. What room is behind that blank wall on the left side of the house to the right of the window? Could you add a small window in an interesting shape and/or stained glass centered there -- or you might just plant an American pillar Arborvitae several feet in front of the center of the blank area. https://gardengoodsdirect.com/products/american-pillar-arborvitae-trees?variant=31264570736682&utm_medium=cpc&utm_source=google&utm_campaign=Google%20Shopping&gclid=EAIaIQobChMI55XFnqi36QIVFZSzCh3ilgqDEAYYBiABEgLYp_D_BwE

Creating a vented rain screen behind siding is a best practice, but not constructed as shown. I would investigate the potential for venting the horizontal void spaces at the corners using insect screen and some standoffs to create vent openings at the corner boards. It won't perform as well as a vertically vented system, but it's an improvement that can be implemented without tearing off all the siding.

There is always a solution however the solution may not be to your wallet's liking. No one here can determine exactly what you need without being there. So many variables involved. I can say I'd never have that small of a KW for 2000sq feet. IMO, you need at least 15KW just based on square footage alone without taking into account the various heating loads. NOLA homes are usually accompanied with large heat losses throughout. But you can't just jump from one KW size to another without having to potentially upside your wiring and breaker(s). Unless the electrical was already set up to handle a larger amperage pull, then that cost will be involved. Then you have to move the air down the longer runs which may require a larger unit. What brand and model is your current unit? You really need to know how long and what diameter those runs are to determine what is now needed. So regardless of any heat losses you still have to move the air to the other rooms. One other thing you can try before dumping a bunch of money. You say the rooms closest to the attic are fine. Are they so fine that you can take some heat from them? Are they receiving more than needed both warm and cfm wise? If so, then you could potentially close off those a little with dampers so more air and heat is pushed down the other runs. Just a thought.