I agree that denying applications based on pets isn’t really discrimination; it’s more about the costs involved.

Even if you get a full time property manager they will not be able to deal with a roof repair situation or any storm damage without your direct involvement.

If you don't have a realtor involved, often you are going to get to live with those things for as long as you own the house. 

@Dan Heuschele I wont mind getting the adu separately metered if it were not for the cost and the time delay involved in doing so.

I’d recommend pushing to get that or get the city involved to revoke their license, both of these firms.

Bookkeeper helps but you will still need to be involved and will need to prioritize providing feedback on transactions on monthly basis. 

Even though we hired a project manager, I want to be more involved in my deals.

For example, you could refinance one of your rental properties at a low Loan-to-Value (LTV) ratio.If you prefer not to involve a partner in the down payment, you might consider asking a family member or friend for a loan.

At this point, is it worth it to get my insurance involved to help motivate the HOA to address the issue or will getting my insurance involved slow things down?

Get a contractor involved early to look at your renovation plan.