All three of your examples are the kind of thing that gets written up.
The inspection looks at health and safety, which sounds like it means big systems and in practice means a long list of small items. A window that doesn't lock is a security item. Missing handrails on exterior steps come up routinely once you're past a couple of risers, though the exact threshold depends on the inspector and local code. Peeling paint is the one to take most seriously, because on a house built before 1978 the lead-based paint rules apply and deteriorated paint isn't a cosmetic finding at all. Whether and how those rules bite depends on the age of the house and the age of any child in the household, and the remediation has to be done a particular way, so that's a question for the housing authority and a certified contractor before you buy, not after.
Heat and roof matter too, but a house with a good roof and a working furnace fails all the time on the small stuff, then passes on reinspection a week later once someone spends an afternoon with a drill.
What I'd add to your comparison: walk both houses with the housing quality standards checklist in hand and count items. The number of small fixes is a real cost and it's knowable before you offer. The thing that isn't knowable from a checklist is whether the neighborhood has voucher demand at all, since your tenant pool depends on households actually holding vouchers who want to live there. Call the authority and ask how many families are searching in that area.
