In general, the idea that water will weep below horizontal siding that has been nailed tightly to the z flashing above the field applied trim of a clad nail-fin window head, is only theoretical and is unlikely to work in reality. Caulking serves no useful purpose at this joint but it probably doesn't block moisture flow any more than the siding does unless some kind of drainage membrane or mesh is installed behind the siding. Also the top of the flashing would have to be lapped under a wrb or adequately and permanently sealed to it. I don't know if either of these details have been used here but since neither of them is usually done properly enough to be effective it probably doesn't matter how the joint is treated. The whole idea of a sheet water/air barrier is probably no longer feasible with modern nail-fin windows, sticky flashing tapes and plastic housewraps that can so easily be assembled to trap moisture against the sheathing. In my opinion, exterior wall construction materials have been "improved" by chemical companies and marketing gurus until they no longer work well. It's time for a modern system that avoids such fussy and easily misunderstood details.

Mine are all scanned. The only non-digital records I keep are the kind which one needs the originals of - death certificates; passports; signed copy of Trust or other estate matters. Are you worried about capital gains taxes on sale of the house - i.e. proving your expenses to offset the gain?

Hmm - I just got notice today from Spectrum that they're doing maintenance tonight between 12am and 6am and to expect our internet to be down for around 15 minutes. Makes sense for them to do it in the middle of the night when most people aren't using the service.

The flashing can match the roof or gutters. The gutters should match the fascia. the downspouts can be the gutter color or what goes best with siding color.