I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

I completely understand that concern and glad you both raised that point about a nursing home, however, I do have a big house and we have casually talked about moving her in with me when that time comes.

If I understand correctly your siblings goals are to sell their rental properties, use the funds to purchase a primary residence they'll eventually move into, and limit their tax liability correct?

That’s okay—what’s important is understanding the "why" behind your investment decisions.While your accountant’s suggestion is a great starting point, make sure investing aligns with your own goals and situation—not just because someone else is enthusiastic about a particular strategy.

Fortunately I have all the standard contingencies.I also question what is a fair price for insurance.  

Than maybe with adjusting the vocabulary to REALIZED performance and UNREALIZED performance, we can start correcting understandings. 

I was going through the rent control laws ( I know, should have done that before purchasing the property ), and a section stands out. https://ecode360.com/30526708#42037155Based on what I can read, the rent control chapter doesn't apply to: Dwellings of three and four units, at least one of which is occupied by one or more of the owners thereof.My understanding is that rent control doesn't apply to owner-occupied multi-units. 

Investing OOS for the first time, and using a TK provider for the first time.I understand I'll be paying (significantly) more for a TK provider home.

They both own thier own management companies as well, so they understand the needs for investors when it comes to insurance.Best,Brad 

They are prompt, proactive and understand property management from an investment perspective.