The extra $100+- a month doesnt seem worth the hassle.

I saved extra money, and made a larger than normal down payment, and used a combination of a private loan and a heloc to swing my first property deal. 

His argument for a duplex is that if I decide to move, I am "stuck" with a duplex that no one will buy and will have difficulty purchasing a new home in the area I move to.First of all, I am not sure why I would ever want to sell (for a while at least).

Which I have heard is quite difficult. I

Although the market can be lucrative, finding good deals in these areas has been increasingly difficult. I

How difficult is it to obtain?

Did we learn anything, yes but alot of half-truths too.Came home and created a Nevada S-Corp and put an LLC under it, assuming we would go national.Property bought was in Calif, so more expense to Foreign File both entities.Started looking into creating my own Property Mgmt (PM) business to control out-of-state holdings.Then I learned:PM requires a broker's license or to be under his control almost everywhereThat stopped National expansionwhich then made the S-Corp and LLC unnecessary (to me; I accepted personal risk)Did get good liability insurance and suggest an extra Umbrella policy if you're going to buy&hold (aka become a landlord).

I figured the extra money through tenant rent and (eventually) investment would be very helpful with my lifelong goals. although I know there will be a challenge of fixing or maintaining the house would not be easy, I am up for the challenge. 

Based on the tone of your post, it sounds like the HOA is having financial difficulty and that may or may not change your strategy.On a side note, I do not believe your HOA will provide any details from the other claims, as that is not public information and should not be shared with parties who are not principal to the claims. 

Its worth the extra few minutes out of your day, especially if there is a mail thief!