Sounds like $15k might be a generally safe bet on houses that look "pretty good"... and obviously upwards from there if adding an additional room.Property management fee: Yes, 10% was my starting rate there, but I have 4 properties in the area currently and my management company has a portfolio rate of 8% once you reach 3+ properties through them which is a nice little bonus.I should have caught the property tax difference!

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. 

I would say your best bet is to attend the next Hoa meeting, ask them how they tried to contact you, and then ask for a “reasonable” $50-$100/month fine.

Because FCRA specifically forbids someone from waiving their rights to protect the information.There are some very limited exceptions.

Directly from Allregs  Fannie Mae's guides:Limits on the Number of Financed PropertiesIf the mortgage loan being delivered to Fannie Mae is secured by the borrower’s principal residence, there are no limitations on the number of other properties that the borrower will have financed.

They include (but not limited to) any loan mortgage payments, taxes, insurance, utilities, HOA fees, etc that occurs during the Rehab period and up until the property is fully rented.