I bet that's more than 300k in summer but we will see.

What willingness have you found HOAs to go for in terms of you verifying that their financials are sound, to decrease the odds of any surprise special assessments screwing with your cash-flow (eg, how do you ensure the HOA is budgeting for necessary maintenance)?

This is Contract Law 101 and I'll bet your attorney will agree.  

Maybe i've missed context on this, but it seems odd to question this.  

My gf and I bet $100 every week and if we don’t achieve the goals we set we owe the other $100!

I am betting there will be sizable renovating, but I could be wrong.

@Bruce Woodruff is correct, painting is probably your best bet, maybe look at a section paint or mural type of effect, to save doing entire house.

This seems odd that you have told them repeatedly and they still aren't getting it.It sounds like they are a whole month late on rent!

I'm closing on a property in North Carolina - and the attorney office that is conducting the closing has had some significant communication issues, and has done some odd things (sending wiring instructions to my lender, expecting them to pass it on to me -- then sending it to me in a PDF, via unsecured email). 

As soon as the hospitality sector, restaurants and the bars are fully open then that number will be back in the 2's, I bet.