Repaint wood siding or cover with Vinyl?

[Dan Taylor]

First Post here. Let me start by saying thank you to all of you for offering your time and sharing your experiences on this forum. I'm happy to be a member and look forward to building solid mutually beneficial relationships.

My question is:

Should I preserve the original wood siding on a 100 yr old 2-unit multifamily or just cover it with Tyvek, foam board, and Vinyl siding?

I'm looking for experience on this one. I've had countless contractors tell me to go with Vinyl, however, the cost is about 3x that of re-painting the exterior. Not surprisingly, all the painters say it'd be a travesty to cover the wood siding.

Relevant Facts:
- This is a complete gut. Interior is down to studs and water staining is visible around most all windows and interior corners. Water penetration is definitely my UTMOST CONCERN here.
- Paint is in really bad shape, peeling all over the place. Caulk is practically non-existent.
- Wood siding is in relatively good shape with only a few spots needing replacement/repair. The wood siding is nice IMO, or at least was 100yrs ago. It's architecturally stimulating with beautiful window trim and crown molding under the soffit.
- The neighborhood is a mix. Some vinyl, some aluminum, some wood, some stucco. In this neighborhood, vinyl siding is considered "nice and new" as most are uninterested in architectural integrity or historical relevance.

Things to consider:
- There's a small single story addition (10 x 15) that will need to be completely torn down and rebuilt (for a plethora of reasons). So, if I chose to stay with wood, I'd have to match it (or perhaps attempt to preserve some of the original siding before demo).
- My original budget called for paint (estimates 3-5k, as opposed to siding 12-15k). But, considering the potential water damage to the BRAND NEW interior, this is a serious concern.
- We'll also be replacing ALL the windows and doors. Again, I'm dumbfounded on this one. Originally the intent was to use replacement windows, but if i were to go with vinyl, the potential is there for New construction windows with proper flashing and weather barrier. However, if i keep the existing siding and trim, I'll need to repair quite a few window frames before installing replacements. I guess it was common then, but it really confuses me: the window frames are 1x nailed directly into the exterior trim, which is nailed to the exterior sheathing. there is no "window frame" nailed to studs directly, only indirectly. So, if the exterior window trim comes off, the window and window frame goes with it.

Considering the challenges I face with updating the windows and matching the original siding (which shouldn't be too difficult w/ standard wood clapboard), along with the water penetration issues, WHAT DO YOU THINK? Caulk it up real good, scrape, prime and paint or go with new construction windows with vinyl?

I never intended for this to be a complete gut, just new carpet and paint (LOL). Amazing the problems you find when you pull up a carpet or two but considering I got the house for a few thousand bucks, I decided a gut was essential and I'm happy i did it for longevity sake as this will be a long term rental.

Thanks for your help and any advice you have to offer. Normally Google, with due time, has all the answers but this one is tough to get an unbiased opinion on. Literally watched 2 house flipping programs just yesterday. Episode 1 he painted, Episode 2 he sided with no explanation either way.