All I know is I'm just looking for strategy help/expertise and not for a company to manage my investments/funds who preferably charges a flat fee vs a % of my assets.

Condo fees are unpredictable, condo boards are unreliable and sometimes unreasonable.

At the end of the day, this is one of those things where it's probably as simple as filling out the form and mailing it in with the fee, and that's all a lawyer will do for you as well, other than send a bill.

You do see re-zoning from time to time, but unless there is a real strong reason, it doesn't happen too often.STR regs are something that, in some municipalities, seem to be discussed monthly. 

@Sasha JosephsEither way California is going to charge you the annual fee - but speak to your cpa and see if it makes a difference

Here in the Tahoe, NV area there were a lot of claims from snow and the insurance went up which drove up the HOA monthly fees.

Alternatively, you could do a flat fee for one or both units.

We have cash in the bank but want to discuss lending options to not drain our liquid.

(I like my original points better, of course, but this is a great discussion.) 

In terms of educating yourself, it would be good to get an understanding first of what, if any, your family's estate plan is, and if there is not a good one, get yourself educated in that area for a continuing discussion with your dad.