She's also worried the tenants are going to trash the properties..etc etc...So how can I convince my wife that investing in rental property is not gambling and is a great way to financial freedom?

One of the things I don't necessarily like about it is that I would need to trust that the current owner makes his monthly payment unless the agreement would state I remit the payment to the financial institution. 

Even when they tell you that the property is sold, continue analyzing and find out whether you would really pay asking price after knowing all the financials, recent repairs, board of association, recent changes in regulations, etc.

I will have to deal with them as they have in-house broker in place.I was actually thinking of suggesting free rent for the first few months to lessen the tenant's financial burden in the beginning.

I guess my question is is this the best strategy or are there other strategies to break even on the first property to be able to be ready financially to buy a second property and keep the first one.

I'm a financial planner that generally advises against SD IRA's to hold real estate when the client can purchase directly in their own names.

My problem wasn’t vacancy or dreadful financials for the assoc, it was the high number of investor-owned units (another reason many lenders won’t touch it). 

I am seeking financial freedom!

I am now 25 years old and very smart responsible financially. have a savings plan in place and have been contributing 20%-25% of all income earned for the last several years . 

My goal is to slowly buy more properites and start my financial freedom!