I don't think WOL works over Wi-Fi and whether you can get WOL from a USB ethernet adapter.
My proxy doesn't attempt to handle security. Most folks use either Tailscale or some other VPN solution. In my case I use the wireguard server in my router to VPN into home which gives me access to the proxy and consequently to the machine.
Entirely agree. Breaking things down, also helps to get mental clarity of what you are actually trying to do.
I think one part why this helps (at least me), is that our executive functions are limited by a working memory for a maximum of about 7 things. Many tasks are actually comprised of many more atomic tasks. Doing them step by step helps to really know what you are doing and not being overwhelmed.
For transactions: you spot fraud, mischarges or subs to cancel. Really a watchdog service would be good here. High effort, low return. IMO. (And a bit of tracking around reimbursements)
For savings: helps you keep an eye on where you’re at by forcing you to reconcile.
It’s totally worth it for a low value of invested time. But, it’s not going to be low effort.