Already have an appraisal that puts our DSCR rate at .85 using long term rent estimate.

It seems as though you might get some of your money back on the refinance so I would estimate how much you'll have "left in the deal" after refinance.

If they’re late a third time, you have a strong case for eviction for habitual non-payment—without risking the tenant showing up at the 11th hour with the money.For your specific circumstances, with only a partial month behind, I would guess there is a decent chance they can come even on rent and it would be a waste of your time.

Wouldn't hurt to look in to both to give yourself the best chance at finding the best loan product. 

On top of that, many policies have become more strict (especially in the last few years) with replacement cost language because replacement cost estimates did not keep up with inflation for a period of time AND/OR replacement costs on many older properties had skyrocketed so it made more sense to calculate replacement values with functionally equivalent rather than exact materials.

By any chance are there any agents on this site from there?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

To improve your approval chances, use rental income from your first property, consider co-signers, and explore lenders that use Income-Based Repayment (IBR) for student loans.

Additionally, if there are any contractors in the Fort Lauderdale area who can provide an estimate or guidance on this type of conversion, I’d really appreciate the connection!

i.e. getting outbid on offers, properties become unavailable before you get a chance to see them, etc...You are not alone!