Should get decent occupancy year round.

there is literally no way this would only cost 16-20k to fix LOL. wishful thinking. i would call this a full gut based on the pics and use $65/sqft for guts (even that is sometimes not enough but it's a place to start). so if this property is 1,000 square feet, we're looking at a $65,000 reno give or take. what did your contractor say it would cost?

I believe I've got enough work to hire a couple people full time year round. 

Did you filter by number of garages, bedrooms, square feet, price?

If i purchase a rental property for $80k down (will have $20k left.. just rounding here), how will i save up enough to purchase the second rental property?

It’s crucial have feet on the ground.

I think it would benefit you to have an knowledgeable agent to help facilitate, negotiate, and walk you through the purchase / inspections and hold their feet to the fire if need be.

They will throw in everything including that you insulted them and your feet smell.

how many square feet?

But you ALWAYS have the option of shopping with your feet.