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BayArea says

2.) When I talk to various providers (Geico, Statefarm, etc), they all ask me how much I want to insure for structure, how much I want to insure for personal property, and how much I want to insure for loss assessment. I tell these turkeys that the amount of coverage I want is heavily dependent on their price. When I ask them to present it to me variably, I get confusion on the phone. Is there some way that I can make things easier on both them and myself in the way that I request these quotes?

Just ask for replacement cost. They will tell you how much the replacement cost is. I have several condos and I just pay $175.00 for each one of them through State Farm for a landlord policy. The master policy has "walls in" coverage.
I also make sure the tenants have renters insurance.

Pardon my ignorance but when you say replacement cost, that's replacement of what?

BayArea says

Pardon my ignorance but when you say replacement cost, that's replacement of what?

Replacement cost of the structure and personal items. The part that is not covered by the master policy.
I admit my knowledge on this is limited, and I don't want to mislead you. If someone knows better, I want to hear it too.

I think that may be part of the challenge.

They don't know what replacement cost is unless I give them a number to quote against. And my knowledge on this is limited so when I give them numbers I am somewhat shooting in the dark.

This condo insurance topic seems very ambiguous...

The other part that people often complain about is that they get a policy thinking they are well covered... until the first time they file a claim.

BayArea says

I think that may be part of the challenge.

They don't know what replacement cost is unless I give them a number to quote against. And my knowledge on this is limited so when I give them numbers I am somewhat shooting in the dark.

This condo insurance topic seems very ambiguous...

The other part that people often complain about is that they get a policy thinking they are well covered... until the first time they file a claim.

Many insurance agents will give very limited coverage just to make the quote look competitive, when it isn't. Look for a very experienced agent - 20 years in the business.
I tell my agent to make sure I have the right coverage. I trust my agent.

Would you be willing to give a referral (privately)?

Would very much be interested in gettin in contact with someone who knows the topic well

I've gotten some pretty bad young agents when just calling in.

I'm located on San Mateo.

Condo is in the Berkeley/Oakland Hills area. Are you local?

Here is what I have:
Auto Insurance - Full liability 100/300 high deductibles.
Home Insurance - Full replacement $5,000 deductibles.
Earthquake - whatever it is.
Umbrella policy $2 million liability.
Landlord policies.
All my insurance is through one company, with an agent I trust. I generally maximize deductibles.

BayArea says

I'm located on San Mateo.

Condo is in the Berkeley/Oakland Hills area. Are you local?

Im in Orange County.

I would buy none of them as insurance companies make a killing on these niche things which are basically useless. It's no different buying a warranty for your new TV at BestBuy as you get ripped off like a mofo.

Keep the money, put it in an index fund, that is my insurance policy.

For 7yrs I just went off the Master Policy included in the HOA

Then this year every owner got hit with a $5000 emergency assessment to cover the replacement of the system as it exceeded what the Master Policy covered.

Now I'm a little on edge...

How much is the condo worth?
Do you have a loan on the condo?
Do you currently have an umbrella insurance?
Do you want one?
Does your renter have a renter's policy?