But if you have a deadline, multiple jobs, or just short of time... you gotta pay to play.

After she/he moves out, follow your state guideline for deposit dispensation, the deadline of which is likly triggered by the latter of the tenant moving out or the lease ending date.  

If they redeem after I do all those things, but prior to the redemption deadline, am I out all those costs or will they get rolled into the redemption amount?

Send a pay or quit notice with a 3 day deadline.

In this situation, I see a lot of investors overpay for a less than ideal asset to beat the taxation deadline.

Is he good with deadlines?

So the nightmare scenario is a huge set of fines rendered long after he's gone & I have no leverage to get recouped.Any advice on how to get the HOA to meet a deadline for a fine decision when there is nothing in the bylaws compelling them to?

What is the deadline for late payments?

And then be disciplined with the execution so you work to your deadlines and budget.Credit Card debit would be a much more expensive option. 

Only offer discounts to tenants that have proven their worthiness.I would give them written notice of the issues and a deadline to have them handled.