I am all okay with an agent offer her extended service but just want to know where the lines are suppose to be drawn.

Ha imagine the emotional rollercoaster of a ride my wife enjoys with that kind of flip flop happening in my head all the time Gutters: So my gutter guy didn’t install my downspout extenders (or whatever they are called) or splashpads (again probably not the official term but better than my first guess of water distributer thinga-ma-jingy).

I have had great success with French drains and extending down spouts into drains or 4 feet away from the building.

Unexpected repair gets done right and an extended vacancy isn't that stressful.i guess my answer is I have no number, or if I do it's fluid based on my lifestyle.

How to do you guard yourself against getting too excited and over extending yourself or making those bad decisions?

Most of them also wanted extended closings (up to a year)  I was ok with about 6 months since I needed that time to make my new SFR home habitable before moving there.I also did enough digging to come up with the mailing address for the LLC that had bought the property across from mine at $740K. 

This way another buyer comes along they have the choice to match the similar or better offer otherwise they lose the chance to buy the property.Additionally have earnest money held by an independent party with the transaction and have built in escalators for more and more non-refundable money each time they go to extend the contract.

Pest control, even when it's bad, is very fixable with a decent extermination and a lot of understanding extended to the tenant. 

Now I’ve asked the seller to extend the closing date and they accepted 7 more days for us to have the lender’s underwriter to review the appraised value.

Give the tenant the appropriate notice and then bump it.I don't recommend extended notices or graduated increases.