Even then, it can be difficult to get contractors to show up and meet deadlines.

You receive the util bill, you pay the bill, you send a statement to the Tenant with the charges for their usage, and a deadline for payment.

But, you likely need to first give notice of non-renewal; then offer your new agreement and terms with a deadline to accept or reject and vacate that is within local requirements.

but I was urged to look more into who is going to answer my questions when the buyer is flipping out and you're on a deadline crunch and you don't know the answer.Who is going to have local answers regarding your market and connection for contractors, etc?

Nothing lowers standards like punishment and deadlines.  

Give the tenant a deadline to make a decision.

Not a problem to wait 6 months in the grand scheme of things (unless it was purchased with tight deadline/balloon debt), but it's unexpected. 

We've seen it all- consistently missing deadlines, questionable cost creep, limited knowledge/service.Actually considering building a team in house to support the deal flow!

So when I bought my first duplex in Fishtown end of September 22, the deal worked well with the true property tax based on the houses value but the house was assessed right before I purchased it and was overpriced (had the house value at $500k when it’s more around $391k) I hired a company suggested by my realtor to help me submit the appeal right before the deadline and it’s been crickets ever since.

You might have to broaden your scope as you get close to your deadline.