So the more we offer to help, the more we are entrenched in everything.

By day, I'm deeply entrenched in software technical support, specializing in automation, troubleshooting, and top-notch customer service.

For buy and hold, I'd go with no - at least not until you were really entrenched at your job.

She got it as part of her divorce settlement years ago and some of the tenants are super entrenched (15 plus years).

These are companies that are so entrenched they can't break free, but have to cut back on what they do...and how well they do what's left...in order to survive. 

Maui has a pretty entrenched property management industry, so, absolutely no issues finding someone to manage properties.What I look at is the 20-50% cut, and rather than what does MY time cost on my property, what do THEY cost ME.I'm still just a small-timer, so the time I spend on managing from the mainland is what makes the entire endeavor worthwhile. 

I have heard so many diff things about why this will not be the same as 2008, but most of these people are deeply entrenched in the market with retirement accounts and over leveraged rental properties and vacation rentals.This is going to sound pretty anecdotal but, I take a walk every night with my family.

This is one of the oldest stories in the book... entrenched interests fighting technological advances that threaten them but offer most people more efficiency and better product for a cheaper price. 

You appear to be way too emotionally entrenched in your business.

You are strongly entrenched in your beliefs and I in mine.