I'm a DIYer and I've just gone through a very similar project (refinish all cedar siding on a 2-story 60s cabin). I also replaced insulation, replaced house wrap, and did a variety of other things that were convenient while I had access to the walls.
1, should I do it (hardy) or the cedar and 2, would it look stupid?
This depends on your budget. Hardy siding is great, looks nice, and lasts a long time. But, it can be expensive. Get a couple quotes for the materials and decide if it's appropriate for your financial situation.
As for the siding you already have, cedar siding can hold up pretty well for a long period of time. But, keep in mind that you'll have to attack it pretty hard to get it down to a surface that's ready to accept paint/stain. Expect to damage some to a point where you'll have to replace them. On the same note, there's a chance you may progress through the project only to find that it's more work than you planned for initially.
If you do decide to try and re-use your existing siding, don't waste time with palm sanders. Get an angle grinder and a couple bulk boxes of sanding discs (40 or 60 grit). You'll need more than you expect. It will leave swirl marks that you'll address with the palm sander after. But, don't use a palm or disc sander to start. It's a huge waste of time and a mistake that I made in my own project. Learn from the pros and use an angle grinder.
I figure if I'm ripping off all the siding, I should replace the particle board with plywood and add house wrap. The way it's done now is with that thin, really crappy stuff and I have a feeling I'm going to find problems
The wrap you already have is likely #15 tar/felt paper. And yes, you will find problems. This would be true with most houses anyway, so don't get too discouraged when they come up.
Some building codes differ on the house wrap requirements. Double check those before you buy anything.
House wrap is very easy to apply with a helper. It's very annoying to apply solo.
Other than cost, any reason not to do the plywood and how thick should the plywood be? Has to be exterior rated too right??
Thickness depends on many factors, one of which is wind load. Plywood for sheathing is commonly 3/8 or 7/16. The grade of plywood depends on your application. For sheathing, CDX seems to be common. Always check building codes for your area. Just because something might be common doesn't mean it's allowable in your situation.
As an alternative, you may want to consider WRB Sheathing instead of plywood. A popular option is Zip System. There are lots of conflicting opinions on plywood + Tyvek vs Zip System. Just be sure to consider your own situation and don't get too caught up in the discussion itself.
A word of advice - be careful that you don't get too ambitious with the project and end up with a house that lacks siding and weather barrier. The steps can be simple, but the work takes time. So, plan accordingly.
should I replace the windows while I do this? My current windows are 14 years old, some don't open real well, hazed up, etc so they're due but the framing of the windows I have is metal and there's no screws on the inside of it for removal.
There could be a reason why they don't open well such as changes in the opening caused by swelling wood, house settling, etc. Otherwise, does your budget allow for it? If so, and if you aren't happy with what's already there, then use the opportunity to install windows that are more to your liking and design preference. It will be much easier with the siding out of the way.
You didn't ask, but if you are exposing the framing, it would be a good time to replace insulation. Buy the insulation that's made for the cavity size. Don't try to stuff as much as you possibly can in there since doing so actually has a negative impact on the performance of the insulation. There are many types of insulation, too. Rockwool performs well in my experience. But, the regular fiberglass insulation is still adequate. There are higher performing solutions, but those come at a significant cost more by comparison.
On another note, if you expose framing, it may be a good time to consider any other improvements you may make in the future:
- running some conduit for low voltage wiring (ethernet, security camera wires, etc)
- run some conduit or other electrical runs (interior/exterior lights, plugs, switches, etc) - be extremely cautious when doing anything with electricity
- any plumbing considerations (installing another sink, bathroom, shower, etc; inspect/replace existing damaged plumbing)
- inspect/replace any damaged studs
Whatever you decide:
- double check your local codes
- make a project plan before you start each project
- keep your budget in mind
- just because you can DIY doesn't mean you have to
- don't be afraid to hire someone to help and/or contractors to tackle certain projects
- don't bite off more than you can chew at one time
- expect that things almost never go perfectly
- check the weather before you tear off siding
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Best of luck with your project. I'm sure it will turn out great.