This strategic move holds promise for generating positive cash flow, which could effectively alleviate the future monthly deficit if I refinance my house. 

You should advise the roommate that they are welcome to submit a request for accommodation but unless they have a plan that would alleviate your symptoms their request will likely be denied.

Many sellers will entertain a higher (or full priced) financed offer to purchase with a Pre Approval letter, since it alleviates some of the unknown variables. 

Under most circumstances like this, I advise my clients to deny the application when there is no way  NOT to lose insurance coverage, but I advise my clients to first contact their insurance provider to inquire about any provisions in their policy that would alleviate this problem. 

Ideally, if you *have* basis in your S-Corporation, you can dissolve it in the same year you distribute, thus you’ll have a cap loss to help alleviate the cap gain.Gain likely won’t be mainly ordinary if the bulk of depreciation is on the 27.5 year or 39 year lives.

Largely we aim for mobile home deals, we've ran into complications and obstacles when dealing with some of the agents so prefer to deal directly with the buyer & seller, but creating a relationship prior as you're recommending could alleviate that for sure. 

Again, we have found the 30 day guarantee can help alleviate this fear since it gives the team time to understand those variables and communicate them to the client.

I am happy to share a form I use that helps alleviate the hassle along with a pdf outline

I don't think investors understand that in many foreclosure situations they are going to lose interest for sure and principal ( very common). the thought that 20 or 25% equity is enough coverage to alleviate a loss does not play out very often in a foreclosure situation.

That'll alleviate a lot of pressure.