CA is brutal when it comes to taxes.I don't give tax or legal advice, but many people believe that holding the property in your name and having a good umbrella policy is a good solution.

I have had a rental property for a short period here in CT and have sold it in 2017.

Did you ever find a solution for a 3rd position heloc?

The main question I keep getting asked is if I’ll do it again.

Quote from @Will Greenlee: I would agree with @Drew Sygit every software has its kinks and this one along with all the other ones started somewhere.. 7-8 years ago Buildium was less effective than it is today, and now it is a lot better.

What other strategies do you know?

Let's say it's a family of 4, do you make them all pay for the aprox $40-$50 screening package?

Yes, that's the way to do it, but I wouldn't rely on a property manager or realtor for that.

I do truly want to hold on to it and I think I'm just nervous to change my manager, though I don't feel it is going as well as I'd like it to.

You can make the determination by examining the mechanical systems yourself and finding out their age or hiring an inspector to evaluate the systems.