But now he is staying so we decided to play the cat card, and told him that per his lease pets not allowed and if he would like to keep it we will need to amend his lease to include additional $100 pet rent plus collect additional security deposit.

If your budget is around $400,000 I would try to find something in Northern California, Nevada or Arizona and play the appreciation game.

Markets that appreciate also have rents that appreciate...play the long game and resist the urge to chase after the best day 1 cash flow option.And you mentioned your obsession...that's a good to place to start.

It seems like if I wanted to buy direct from the HOA, I could play the scare tactic card.

You can:Go to other markets, or;Find motivated sellers or;Adjust your financial criteria to reflect market forces (either directly or through using some value-add approach after purchase), or;Hold off expansion of your empire until the Gods (market forces) see things your way, or;Pack it in and play the stock market.BTW, drop the "two months" self-imposed deadline: You will wind up doing a deal for the sake of doing a deal, trying to convince yourself it is "good'" not because it actually is "good."

In your case, if you have $100,000 on the sideline I don't know if I would necessarily invest all of the capital unless it is in at least a B neighborhood and play the long game, rather than invest in the more volatile markets and swing for the fences.

The crazy deals often come of the 'crappier' houses that need lots of work.I think your biggest challenge (from what you have told us) is that you probably don't have the money necessary to play the 'foreclosure game' - at least where I'm at.  

There are companies out there offering low interest rates for 30 year fixed mortgages so you would not need to deploy all of your capital into one rental property and then play the waiting game for when interest rates drop. 

@Darrcelle McGinnis wow, I should play the lottery today:)Couple of thoughts:1) Don't burn a bridge with the contractor friend.

The longer you play, the better you become.