Welcome rembless. It sounds like the pressure is on, cashflow is tight and you have lots of ideas. Perfect! Here's my 2c.
Complexity is the enemy, so try to tackle one thing at a time and keep it simple. Also your needs will change, so don't chase automation too much if a manual or assisted workflow will do the job for now.
I wouldn't bother with budgeting right now. I would focus on 1. tracking current status and 2. short term forecasting. Yes I think hledger could help with both, and you could improve on that very tedious manual process.
Eg:
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Track current status. Regularly download and import bank CSVs, as you're doing, and make sure your reported current balances agree with the banks' web UIs, so you can feel confident about your reports. Don't bother with the status flag, or at least keep it simple (I have never used pending). And don't worry much about categorisation, you can improve that ongoingly.
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Forecast. You don't have to use hledger's --forecast for this, but I would. Convert your list of expected transactions to forecast rules, ie "periodic transactions". You can have them recur monthly, or be non-recurring one-offs. Model the next month or two that way.
Here's how to print the transactions forecasted in the period from 15 days ago until 30 days from now. (The 15 day overlap helps make sure you see transactions that happen a little later than expected, which might otherwise be suppressed by the latest-dated entries.):
hledger print --forecast=-15days..+30days tag:_generated
Because you are importing bank csv, I think in most cases you'll use --forecast just for looking ahead, not for generating entries to be recorded in the main journal. (Except perhaps for non-bank transactions.)
Here's how to show the daily balance in all banks, based on this month's past txns and then forecasted future txns:
hledger bal -HD -bthismonth --forecast assets:banks # --drop ... --transpose
or to see the recent and forecasted balance in one account:
hledger areg -bthismonth --forecast assets:banks:bank1:checking
I think just this could be useful, and I hope it helps. If you'd like, join one of the chat rooms to get more questions answered. Good luck!
PS: some of the details are easier to see and do in the heat of the moment, than to describe "cold". Here's another one: if you are using the commands above, and the print command shows a transaction falling into that past 15 day window, then you would want to take steps so that the following reports will include it, for a more accurate forecast: eg adjust its forecast date to tomorrow, or record it in the journal at least temporarily.