I have a healthy rehab/unforeseen issues allowance budgeted, and have set my max bid, but am hung up on the post-auction/closing routine.

Books, podcasts and REIA meetings should all be part of your regular routines. 

One of my clients routinely buys assets in the 25 to 40k  range and sells them north of 175k but they also gut them to the studs and put 80 to 100k into rehab. 

An asphalt shingle reroof is not rocket science but pretty routine, and some inspectors even note that roofs have to be repaired or replaced in some transactions (or is it flat built up, roof, etc). 

My idea is that the CPU could upload routine logging data to me maybe a couple of times a day, and send me a text message for alerts (water running for a long time, temperature falling near freezing). 

I have never had to file a claim, but I have found them to be extremely friendly and responsive during any routine inquiry. http://www.affinitygm.com/

But, should probably make it routine. 

As you've probably gathered from my day to day routine, I'm starting with wholesaling with the intent to transition into fix/flip properties.  

There was a time that it was a huge deal, and with scale it becomes routine.

I was the acting agent on the property and took a commission on the property but, again, I purchased this for myself.2) I routinely go from home to work (actual job) and then from work to either one of my properties as a property manager or to meet one of my clients to look at properties, etc.