His broker is being a pain and said I ought to seek legal help, although I stumped his broker when I told him I have his agents text to me essentially terminating our relationship (as mentioned above).

Another investor, that has already done the hard work on vetting lenders (and other vendors for that matter) will significantly reduce your pain in this area.  

Also, I have no idea what the oven is worth or how much to file a claim for, so I suppose I need a stonemason to come out and give me a quote...What a pain in the butt!

Is the tenants a pain in the ***?

@Shiela Roberts, I agree the time and pain dealing with the contractor and the ROI may not be there.

Plumber couldn't complete sewer scope because there's no clean out and getting permission from seller for anything has been a pain in the *** (at least that's what our realtor says).

The earnest money eases the pain and frustration of that, but it's likely that they'd still rather close with you.  

Is it just to be a pain or is there a deeper rooted issue causing some uncertainty. 

Hi there, I'm looking to better understand the home maintenance space. I wondered if contractors spent significant time and money finding jobs. Do you spend a lot of time visiting job sites and providing bids that end...

It’s a pain at year end for taxes if you didn’t keep up with monthly entries.