For example call the water company and the power company to find the average monthly costs for the last six months.

In BC, there are limitation with percentages that a landlord can raise rent each year and once the lease is up it will roll month to month unless the tenant wants to resign another term. 

My time is very limited with my full-time job, and feel it might be best if I have all the information in one place and a resource along the way. 

Based on my very limited research the west side is probably the best, however many of the multi families are in the downtown area near the border and in less desirable areas.

If there is an HOA it has to be registered with the state (in my experience which is only TX, CA, CO) and the by-laws should be recorded at the county recorder's office, again in my limited experience this is always the case. 

Seems that as long as I build the cost into my numbers up front it'd be a good way to limit my exposure to tenant struggles and take advantage of the company's experience and knowledge of the market.

Looking to explore options for owner occupant lenders outside the conventional limits that borrow in Chicago to high credit/income individuals with under 20% down.

As far as the Umbrella policy goes you should look at an Umbrella Policy as "excess liability" or "secondary coverage" meaning the underlying policy (home or auto) pays first in a claim situation and if the claim exceeds the limits of the underlying policy THEN the Umbrella kicks in.There are companies that will sell you an Umbrella policy without requiring you to buy another policy from them ...but...they still want to verify your underlying coverage on the home and autos.Geico is an Auto insurance company first - they broker out the homeowners policy to other companies which is why you may not be getting good advice from them...plus it's an 800# and the kid you are talking to may not have any real world experience in what you are trying to do so can't think of any solutions.Try reaching out to a local independent agent or a Farmers agent - Farmers has options to put all but one of your autos in "storage mode", and should be able to combo that with your home as a landlord policy thru Foremost then set up an Umbrella policy for you on the entire package.

We can also only charge $126 if we don't have receipts so for the work I did I was limited to that amount and let me tell you I was in there for 5 or more hours.  

Figure 10% higher tax (cap gains vs ordinary) and SE tax isn't too bad If someone is over the Social Security limit however still sucks paying it.