@Chris Aronson Those numbers don't seem unreasonable, although from a cash flow analysis perspective you can remove your own utility bills from that number (those are resident figures and you should care about them for your personal budget, but they are not important when evaluating the property - a future tenant will pay them!).

But if you ever end up in court, the judge (and law) will say your agreement is unreasonable and it will be thrown out.You're asking if you can create a lease agreement that is reasonable, while owning rental property in a state that is unreasonable.

If you did end up in court and explained that you were going to be three days late with rent, the judge would find in your favor and you would not be kicked out.Your landlord is being unreasonable to not wait three days.

What you claim to be unreasonable is actually the normal process that all Section 8 landlords participate in. 

Are any of my assumptions unreasonable and should I re-evaluate? 

Mainly you'll want to make sure that if you're going through your bank it's on your timeline in collection dates, and that the fees are not unreasonable. 

The comps I looked at say a ARV of around 507k isn't unreasonable.

If I am still planning on living in the area (within 10-20 minutes), is it unreasonable to think that I can continue being the property manager after I move out of the property?

Am I being unreasonable in expecting him to rent the equipment and me pay for the completed job or to reimburse him after the equipment is returned and there is no longer any liability for it?

While it isn't common, people do back out prior to move in and I think it is unreasonable to think they should lose the entire SD.When we collect funds prior to move in we have them sign a separate document (lease is not signed until move in day or very close to it) that spells out what that money is counted as and what it is converted too if the lease moves forward and if they back out.