It's REALLY hard for owners to cash flow paying a PM at all, much less 25%+.  

If it's working as an LTR and you are cash flowing, I'd be willing to bet that the juice won't be worth the squeeze in converting them to STRs. 

Pay cash and then after 6-9 months do cash out refinance. - in this case, I will have more time to shop around for better loan terms/rates etc. 

Ask @Dave Foster for any 1031 questions…But I’d start with these…Are you planning to pay all cash for the replacement property since it will probably be either impossible or expensive to get the loan in the LLC’s name.Why are you putting the property in an LLC?

Cash out refinances of existing properties might be a great option depending on how those parameters look within your portfolio.

If I buy my home in Michigan first that cash flows, I can save that money and buy the Florida property as soon as I have enough saved.

Not by obtaining a judgement against an individual or an LLC for that matter because all they have at that point is a piece of paper, not cash proceeds.

Purchase price: $440,000 Cash invested: $20,000 4bed 2.5 bath 1811sq ft - New build from D.R.

I get more cash upfront, cashflow after my cash-out refi, and I net more on the sale because no realtors involved.Young family that the husband started a business 1yr ago so couldn't qualify for a mortgage, but they wanted to buy a home. 

You've been able to save up and have $50K in liquid cash.