Could be a guideline issue where an overlay won't allow more than 4 properties, could be he writes everything off and you're expecting them to add back in something that they won't or it could be; not having the taxes, I'm not sure what it could be.You may be better served to go with a DSCR loan. 

The writings on the wall.

Could I write the name of my IRA into the wholesale contract as the Buyer and issue earnest money from my IRA?

Since you do not own the property yet and are just gathering information, most likely they will not spend hours on writing a bid for free, and most good contractors have more work than they can handle right now.

The standard lease states that they have to ask the permission in writing if the person is going to stay for long duration.

They may not take it at first, but as the writing is on the wall they may take it. 

Most Insurance companies will not write a Homeowners on a non-owner occupied house.  

You need to contact your insurance agent and let them know what happened and get from them in writing what needs to be done. 

if i wanted to go with the simpler option, would I have to get it in writing, or can it be more of a gentleman's agreement?

just went through the Bully session and the arbitrary disallowing of write offs .. very frustrating.