We wound up doing that with our house without knowing that was what we would wind up doing.

In the one friend with 1 rental property and his own business in example mentioned with a CPA he wound up getting audited and having to pay penalties and back taxes.

It's anyone's guess but time heals a lot of wounds in buying RE...I bought my first 'flip' in March of 2008 and rode the value down over $150K, lost easily $10K on rent learning to be a LL and eventually sold that home around 10 years later for just about what I originally purchased it for.

First brokers would not show me deals; then I went into contract on some bad deals out of desperation, which then did not close and I wound up losing a lot of money; and then I switched markets at was at zero again, with brokers not showing me deals.I eventually hit upon strategies to get me over the hump, but getting started was hard.What has been your biggest obstacle?  

I wound add Avery's book to this. 

It will happen: "Time wounds all heels.

So while I kicked my (self inflicted) wounds I studied ecom, and later DTC business. 

I wound up going in a different direction and did not pursue the issue.Bill

I write all my letters myself... now keep in mind my letters are written to only properties I want to buy for myself.... but I've wound up wholesaling two from this campaign.

We wound up with an umbrella coverage reduced to $1.5 million using commercial.As an interim measure, I would keep the $1 million on the individual policies, take your time searching for the umbrella, till you find one suitable.