I understand that it is a gamble and that if I use all  the right tools and do my homework, I will minimize my risk and will be successful.

But most of all, I feel like it's a huge gamble. 

I think I could have paid $350 for the entire year, so its a gamble.

Will you take a gamble and pick shrimp and try it?

Anything less than that is risky and gambling.

It could appreciate but I consider that gambling.

We are obviously very spoiled with the gain we have built up in this property, we were very lucky, at the right place at the right time, gambled spending a lot of savings to make this happen and have put a lot of physical sweat equity in over the 4 years.

At a high level the purchase process went well but i haven't been thrilled with property management.

Include a due diligence contingency that will allow you to back out for any reason (including just not wanting the property anymore).Keep in mind that your agent may not be thrilled with you doing this, as it makes him/her look bad if you consistently back out of deals, but legally, that's how you deal with the situation.

Motivation: appraising is boring, it is a job even if you are self employed, commercial appraisal is not scalable, and does not create wealthRE investing creates wealth, there is the thrill of the deal, and I want to be an expert in finding deals before I make my own investments.