We have a 1960s construction home with aluminum siding that needs to be fully repainted, plus some minor repairs done to the siding. Honestly, the siding looks kinda cheap to me so I'm not in love with it to begin with. I'm hoping this will be our home for the next 15-20 years that the kids grow up in so I'm willing to invest some money for a durable, quality product. However, after fixing up the plumbing, electrical, and foundation, my wife might hurt me if I propose to spend more money on "not fun" things.

A couple of concerns I have with repainting the siding: 1) if a pressure washer is used, could there be water penetration; or if a pressure washer isn't used, it seems like a super tedious/expensive job. 2) how likely is the repainted aluminum to hold up long-term? If it can be done well, hold up over time, and is significantly cheaper, I'd consider it. I've asked for one quote to have it painted but haven't heard back yet. Any recent experiences or recommendations? If replacement, should I be looking at Hardie or something else? I'm assuming resale value would theoretically be a little higher if I replace, but I'm not counting on any serious ROI.

Also, we have two very young kids and both parents work so all work will be contracted out. We have no time/desire to DIY.

I'd replace it with LP if it were mine. I don't have aluminum or vinyl siding but I have to work around it with roofing frequently. Aluminum just isn't durable and if you get hail of any size, it dents up like a golf ball. If yours is in good shape, then washing it and painting it should be a bit cheaper but I can't speak to how it holds up. I can only refer to photos of vinyl, aluminum, and Hardie after golf ball sized hail that I have for my determination of "robustness".

Regardless, if you change to anything else, it has to be painted so, there is no way that's cheaper than just cleaning and painting what you have.

Painting aluminum isn't easy. It takes a lot of prep work for it to bond well. If you do decide to have a contractor paint it, have them explain their process to see if they're used to working with aluminum. If it were me, I'd avoid going that route.

ETA - could depend on faded paint vs flaked paint

Yeah, the first contractor we talked to said he'd have to "do some research" on how best to tackle the project. Didn't exactly inspire confidence (and still waiting on that bid). We have faded paint around the entire house, and bad flaking/peeling in several areas, though not pervasive.

Although I'm sure it's not a major offset, I was wondering if *potentially* the cost of painting a new and more common product (Hardie, LP) would be cheaper in a vacuum than cleaning/prepping aluminum carefully.

I second Jason on replacing with LP. That's what I did on our house that had vinyl siding.

BTW, there were several reasons the VS was installed as there were many areas of rotted wood, etc. that they covered up with the VS!

Sorry you got screwed
Confess to wife ASAP is best
TAMU aka Midas w/unlimited funds & engineering w/mistakes ala a chem.lab.trials tried many sidings on Southside-on-campus-married-strudent-housing in-the-day ... even w/REDWOOD stairs in the budget!
Steel siding failed first
Aluminum failed as this humidity flexed it to death
Vinyl was employed, even cattle fences used it, beside the Fire Marshall calling it Solid Kerosene haha

Aggieland does best with PRE primed Hardie plank/panels/soffits/fascia but still needs painting as soon as brick doses, maybe a bit longer with ideal primers

Agree with the savants above: LP IS ideal so consider your location, humidity, exposure and then warranty, as well as its 1st costs savings in labor

Wife ... what to do? Maybe replace the most exposed sides at a time, then vacations between sides?
Find a richer wife that LOVES this house? sorry, kidding

Or SELL if for a profit due to location and BUY a something with fewer gremlins? My son did ...

I work in the building materials industry. I also second (or third) the LP here. The 1960s siding would be very difficult to match and make it look right for 95% (+) of contractors. An alternative would be Certainteed. In the Northeast Provia is also excellent. I personally hate Hardie, Its find once it's up but it's difficult and dirty to install and if anything goes wrong with the installation it's a pain.

There are some steel sidings available (with wood grain and all that jazz if you want that look) that are excellent as well.

The other thing is that the back side of what you're installed to probably also hasn't been updated since the 60s so that's also going to help a lot. Close penetrations, repair, etc. Will probably be as important as the siding.

I get the non-fun thing. I'm going through that with my wife currently trying to explain the importance of attic insulation over a bunch of built ins or redoing part of the kitchen right now. Good luck!