Could it bring a added level of security that could raise the rent 10-20 bucks a month?

To me, this was "The One Thing" I could do by the end of this year to take my real estate business to the next level.  

If you want to dig deeper into my background, check out the link below.

Being a low level marketing guy, I knew both sides of the equation for the specific company I was working at and the market we competed in. 

Best I can tell from previous posts on the site is that if you are having a problem with your DTI ration transfer properties to an "entity"(this is the usual word choice with little insight into what kind of entity the poster is referring to) However, when you dig a little deeper, it seems to be that even if you own property in an LLC if you sign a personal guarantee (which they pretty much always make you do* it all falls to you in individual, and therefore counts against your personal DTI ratio, which at least for this, seems to defeat the purpose.* it seems if you have an LLC with 2 years of tax returns, you can actually have the business get the mortgage, and not have to sign a personal guarantee.

The reason is often cited from judges ruling on the enforcement of those instruments has to do with recognizing that the buyer/borrower is actually earning equity and is granted a greater level of interest in the real property than that of a typical renter.  

I've taken some courses in analyzing investment properties, produced APOD's, noticed the drawbacks in how the typical Cap Rate is calculated, and dug deeper to find four-square and the mortgage constant. 

That has nothing to do with your skill level or with you at all.

But if we assume some level of vacancy, which all reasonable analyses should, shouldn't that affect the amount of reimbursements as well? 

I feel like i'm in about the same spot. have a small handful of rental properties. done a flip and now feel like its time to bust it up to the next level.