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@WJB For your 2nd suggestion, this can be accomplished by setting a Custom or Average spending target (you can include a buffer too) in your Other/Projected Spending bucket for future months (see snip below). For current month, these expenses will be represented by the Other Spend bucket and can be monitored against your "Left this month" balance.

For your 1st suggestion, in Reports you can applies filters such as picking one category and then in Advanced Filters you can also apply a "Bills & Subscriptions" or a "Not Bills & Subscriptions" filter. This can be used for figuring out your burn rate in this category that are already setup as Bills versus how much you need to set as the Target in your Planned Spending section of the Spending Plan. See snip below for my example of that filtering in a YTD view with my Pets category.

Also in your Spending Plan, you can set up the Planned expense series for that Category to roll remaining balances (see snip below). Having your recurring expenses setup as Bills/Subs for this Category of importance and accurately setting the target amount(s) for this Category in your Planned Spending will ensure your Spending Plan has accurately planned for the category.

And finally, you can set up a Watchlist for that category as a way to monitor the total category spend on a monthly and YTD basis. It'll even show you in the current month not only your total spend so far but also what upcoming Bills/Income for that Category are expected. Here's a snip from the Web app version. The mobile app view has a bit less information and less history and oddly enough shows an "Average" line as the angry red line and a almost invisible dotted line as the "Target" line on the graph. But both app versions do the job. Also in the Transaction register inside the Watchlist, you can click the 3 dots and apply a Filter that says "Recurring is True" and this is a workaround way to see how much was bills vs not bills in a month. Would be nicer imo if they'd just setup the graph as a stacked bar chart that automatically showed that Bills vs Not Bills split in each bar, but que sera for now I guess (would be a great feature add! but would also get complex for Watchlists with multiple Categories assigned…Tags may be a better workaround…). Using the Target in your Watchlist would give you the monitoring capability you are asking for and combine that with an accurate Planned Spending projection for that category and that should be a decent workaround to get you started with what you are aiming for. I can't save you from having to do some math. But I think this combo of tools may help make the math easier at least.

A few more thoughts on the layout:

I wonder if the Bills section shouldn't be named something like Payments, which would be broken down into bills, subscriptions and transfers (many of which are credit card payments). It would be more logical, I think. Also allow users the option to view those 3 sections in a list segregated as Bills, Subscriptions and Transfers.

Planned Spending ought to explicitly say (excluding payments) so that new users see immediately that it won't include those.

Other Spending ought to be Unplanned Spending. But most of us just mark those as one-time bills, which is what they often are.