Ultimately, I just want to be in a position where I can help others who may have started out with unfavorable odds and be a difference maker for people.

Your experience with them may change materially through no fault of your own and then people will look unfavorably at your advice in the future.  

Wait until you have the required savings to purchase the property, but don't forget that the longer it takes to save, the longer it will take to find a deal, start an income stream, build equity, retire.After gaining some insight on this thread, I think #2 or #3 would be the more unfavorable options. which one being the worse decision depends on what your 401k offers and/or how good of a realestate investment deal you have.

So you take some element of risk relying upon it unless you go to the time effort and expense of requesting a ruling in your own capacity.One final caveat, it sounds as if this property would only be partially eligible for home exclusion treatment (since apparently only part of it was your princ res) which may create a number of other potentially unfavorable tax issues not to mention the usual issues of having a corporation (even an S Corporation) owning the property.

An adverse action is any action by a landlord that is unfavorable to the interests of a rental applicant.

There are so many variables in any situation that cannot be fully controlled, but if you have the right framework for decision making than the probability that your outcomes will be favorable more often than they are unfavorable goes up. 

I am trying to better understand the methodology and analytics used by the appraisers to avoid unfavorable outcomes.

The HOA may have a lot of baggage (lawsuits, unfavorable rules for owners, etc) that could make it challenging to sell to prospective buyers. 

If they are appreciating, that's good, but if you expect depreciation, then you could wind up with an unfavorable equity position.If you did do it, putting any profits from the new rental acquisition and any others you can into paying off that Heloc early would only help you in the long term. 

You could be stuck in a very unfavorable situation here that takes forever at your expense .