Work with seasoned professional and drill down on all your options. 

DSCR lenders will have different rules on seasoning (i.e the amount of time between when you bought the property vs. when you closed on the refinance) for how much cash you can pull out and whether or not the appraised value, as opposed to the cost basis (purchase price + rehab costs) can be used to determine the loan amount (i.e LTV * appraised value = loan amount). 

My plan is to learn and work with seasoned investors.

It depends which resort the property is in, if you are using it yourself over peak seasons, and if it’s a townhouse or single family house.

I understand that there are multiple paths I could take, such as rentals, flips, or wholesaling, and I'm trying to figure out which path aligns best with my goals and current situation.Here's my question for all seasoned investors: What would be your first step if you were starting your investment journey today with the knowledge you now possess?

Yes, we have a no seasoning period product. 

You could start an HVAC company that does installs and/or does trouble shooting when it's peak season.

He is a CPA in Cincinnati, although since it is still busy season for him he might not be freed up for a few months.

The deal is a short term rental in Florida so the returns are very seasonal.

I'll probably connect with you when I'm a bit more seasoned.