There are some guidelines that matter.

If lenders are telling you you're over-leveraged, it probably means that you're too leveraged for them to be able to make the loan under the guidelines of Fannie or Freddie (or whomever else they plan on selling your loan to). 

NOTE: It is not HOA guidelines to have 50% owner occ. it is the financing (perhaps government guidelines) industry.Any ideas of how to finance this as an investment? 

You may be able to get the property for a low price, but it's a steady gamble depending on how far north it is.

While looking through the pre-approval guidelines on Investopedia & Quicken Loans for an outline of what I need, I noticed that it will be very hard for a bank to verify my credit history and pay history since it's so short. 

Timing any market is a gambling mans game, some will win, but most will lose.

If an investor already has 3 properties in their personal name and, say, 20 single family properties owned in LLCs all with commercial mortgages... is this investor then eligible to purchase a 4th property with a conforming mortgage in their personal name according to Fannie Mae guidelines?

I'm reading Gene Trowbridges book on syndication and realizing there are some potential fine lines in defining how much active management I'm doing versus the other team members, and how that may imply that I need to follow SEC guidelines.  

And we have guidelines in what we choose to offer our clients (which is entirely based around their investment goals and criteria.)3.  

You need a few simple guidelines to help:1.