I just don't know if my DTI would allow for a second HELOC on another property if something disastrous did happen - like an earthquake or something (which did happen here 2 years ago).  

This mindset allows them to learn from each step and mistake, improving over time.

and Lakewood allows STR licenses on primary residence only. 

I'm not sure most brokers would allow people to do both, but not sure about that.Personally I have more than enough to do on the real estate side, I don't need to complicate it any more by adding mortgage. 

It was quite deceiving actually until I wrote it all done and summed it up.Because the two that your are intersted in are franchises, you ABSOLUTELY need to check out the individual brokerages. 

I think I am suppose to now look into every title policy with some special working that would allow it to move the property to an LLC without affecting the title insurance . 

Don't be another one of these individuals.

I am a part of an LLC with 3 individuals in the partnership.

Reporting each property separately on Schedule E is generally the correct approach, as it allows you to accurately capture the income and expenses associated with each property.

So the mortgage companies and the IRS set the exact same threshold for being a second home or being a an investment property.My CPA however has advised me that there are caveats for doing repairs, or periodically visiting to inspect it, that allow you to exceed the 14 day leisure limit.