My question is, how do you know whether or not you're over-extending financially.

My first thought is you should have extended your due diligence period if you didn't have all the information you needed to make a decision by the end of your due diligence time period.

I ask my property managers to please ask the tenant to let the property manager know if they are going to be away for any extended period of time.

I'm considering a cash out refi to bring it to about 40% equity or 60% LTV and extend the mortgage to another 30 years at 4.75% fixed and take the cash to use for my first BRRR.

Hi @Amy Silverman - I'm in Castle Rock, but I was born in Bay City, and still have a large extended family there. 

The scenario of keeping the house as a rental could have lead to your story of what it was like to fire 3 property managers because of costly extended vacancies and how one bad tenant did $XX,000 of damage to the place?

One thing to consider would be simply getting a contract for the purchase with as extended a closing date as possible. 

Sounds like an opportunity for an extended conversation.

In my market the seller is typically allowed to extend closing with no re-negotiation only due to title issues, and the length of time this is possible is specified in the contract itself. 

Typically a bank will not extend credit to your business if it has only been open for 2 months.  1 year is typically their limit.