We had a random roofer come by and try to get on the roof and a amazon driver get to close to the house so I posted more signs to stay away.  

IS it first to bid down to 0% wins or is there a tie and some random selection from all of the people who bid 0%. 

And there were a few random smaller esthetic issues inside the house.Then randomly in late August, MW calls me and says he has found a tenant willing to pay $1000/month.

That is a gap of $41.67/month extra you could be getting if you went back on the market.If it were me, I would compromise and raise rent to $1,213/month or some random number under $1,300 to look like you did some mathematically formula that makes sense. 

last year I did my taxes with a random HR Block person as I was doing no fun!

But, the half bath it is counting is a random toilet in an unfinished basement, which would piss off potential buyers.  

I would personally find long term tenants so you are not dealing with random new people every day. 

I definitely don't want a random sink hole in front of the property!  

Technically I'm just a random kid with some properties. 

If you want to be successful, just randomly picking vendors takes a lot of time and effort.