What, if any ways have you all dealt with, mitigated this issue? 

The Florida Department of Business and Professional Regulation's Vacation Rental and Timeshare Project Licensing division issues licenses.

Bigger Pockets is a great place to learn and seek advice from the countless other investors who have Failed/Learned/Succeeded in the areas you are investing.I just joined the BP Community recently myself, and in the week I've been here, through communicating with others, have refined my approach and business plan in the area in which we're investing.Dive into the forums, take advantage of the resources under the LEARN tab up top to the left, ask questions.

So, what we do to get around the seasoning issue is give a bridge loan up to 75% or 80% with the cash out.

and was there any unexpected issue?

I'm having the same issue now about this.

Another issue is that the property ARV is 85k, and with most DSCR lenders minimum loan amounts being 75k, the rental won't qualify since the loan amount I'm seeking is around 60-65k at 75% LTV.

From my experience, people are blinded by the extra 50-100-200 dollars of extra cashflow a month and often don't realize that if you have a good tenant that pays regularly without causing issues, it would sometimes take another 3-5 years of a new tenant at the new rate to make up for the vacancy time of the turnover.

Constant communication is crucial.

At this stage, you don't have to go to all that trouble.LLC's are great for protecting you against contract issues.