It will allow you to roll existing retirement funds into the 401k (save Roth IRA) and self direct those funds.  

Lately we have been selling off the smaller properties in the portfolio, rolling those into bigger or nicer units with a 1031 exchange.

Currently the options I'm looking at would all have me keeping employer HSA for ease of payroll deduct but possibly adding other HSAs that aren't for adding contributions, but just for rolling over funds and investing.

I would say you're rolling the dice with that neighborhood and the street trying to push LUX.  

Now let's say one or both people making the purchase owned a condo previously where they roll over the proceeds/equity into the new purchase and put 40% down.

The bottom line was that tax strategizing would only have made a significant difference the year my partner and I got married.Finally, I was told, in their company's words that they are the "Rolls Royce [of taxes]" for real estate investors.

Every property will bring its own lessons, so just be ready to roll with the punches and use what you learn to make your next investment even better.

Quote from @John Burke: Quote from @David CherkowskyNot necessarily that you'll have to bring money to get the LTV down but you will have closing costs on the new loan that you should be able to roll into the new loan.Do you have other debt that you can pay off to get your DTI under 50% instead of putting 20% down? 

But that's just me I guess.Now Travis knows someone who would regret that.Haha, I hope you both can roll with me here.

You just mitigate it as best you can, carry good STR insurance and roll the dice!