There are pro's and con's for both and it is just going to depend on which property type is going to align best with your long-terms goals.

That said, we were confident doing this because it aligned with our 1) Goals and 2) StrategyThe big leg up you have now relates to your credibility.

If they lose $50,000 on an investment, that's at most 5% of their total net worth, assuming they just barely qualify.Most sponsors I've dealt with qualify their investors on their Accreditation status AND temperament, risk tolerance, alignment of interests, etc.

I got the condo for $375,000 on 5/24/2018 and want to start aligning myself to make another real estate investment, given the current home values this would probably take a few years but I want to start educating myself now.

Zoning and permits and the moon and the stars and the ARV appraisal need to align, but yes this is possible. 

I find that buyers have to be more creative on what they are  wanting out of a property and to think about alignment with areas that will turn over and bring land prices up.

Aligns well with my vigorous nap schedule. 

I'm not advocating to rationalize and flex on your criteria, I'm  advocating for deliberately discounting it because it's your first, acknowledging the context of your situation and setting a strategy that aligns to the amount of hustle, education and proaction you are prepared to take.

Sounds like the stars all aligned for you! 

Align yourself with expert people with doing 0.001% deals and you will be ok in a correction.