I do generate some sort of income on this property in part of that I am renting a room out to a guest, but I do not want to bank on this person to keep me afloat.

Most of those programs have some sort of affiliate/referral program.  

Anyone have experience with this sort of workers comp coverage?

I don't think he is really balking at it so much as I live in a place with a lot of well meaning 'hippie' types and they just don't understand or believe that these sort of things are important. 

In response to Mr Ramsey's quote, assuming I'm understanding it correctly and it's meant to be "sail" not "sale" (if it is "sale" it may be some sort of play on words that's going over my head), I think the partners that started companies like Edison Electric, Warner Bros, Hewlett-Packard, McDonald’s, Microsoft, Apple and Google might have a few things to say.  

In my studies I've learned that these large corporations create dozens upon hundreds of subsidiary companies to bid in a sort of umbrella fashion, doing so by flooding the auction site with bids to ensure success, and in turn bidding down the percentage rate (it doesn't matter that they are getting .25% return, because they bought 800 at a time type mentality).   

They are a sort of hybrid rental turnkey/ property management company with realtors and renovators.

@Jay What sort of numbers did you put in front of the HMLs that you tried already?

I know there are new rules for payment processing that requires them to do some sort of reporting.I would think just document everything and if something should come up you can show that your sister reported the income and you are just managing it.

The seller said they would be willing to talk about seller financing but would need some sort of down money, and I told them that was fine as long as we could come up with some numbers that work for both of us.