Ive lived here my entire life, and never in the same part of this city. 

I also never signed rental agreements personally. 

I personally prefer the various options and tools and I especially liked the way it is laid out.

You should be getting more personal, not less personal.

@Troy Fisher was very helpful with providing a good contact and I had a 30-minute conversation with the person.  

These same owners also have no problem paying an attorney or CPA $150/hour or more.Many owners also don't respect their PMCs and try to treat them like a personal assistant at their beck & call.

While rental demand is going down, there continue to be more people purchasing properties for personal use in turn causing there to be an overall shortage of rental units available in season.

However, it will likely lower future cash flow so it is a time-value of money play (and perhaps income tax bracket matching... ie, big deduction during a one-off big income year).Two properties... one with cost seg and one with out will have the same depreciation taken at the end of its life (27.5 or 39.0 years).Also keep in mind that STR usually requires 39.0 years of depreciation for the primary building asset.

Feeling fear is always part of the process when you're purchasing likely the biggest asset of your life. 

Whether it’s worth it depends on your personal goals and financial situation.