Firstly, it's important to point out that Pismo Beach, like many other California towns, has imposed stricter regulations on STRs in recent times.The city has drawn a distinction between three types of authorized 'Less Than 30-Day Rentals,' specifically a "Short Term Rental," a "Vacation Rental," and a "Homestay Rental."

On the other hand, leverage could allow me to acquire multiple properties faster.Considering my circumstances (unknown target market, family support in Fort Wayne, long-term goals), what approach would you recommend?

Assessing the current market conditions and property values in your area can provide a clearer picture.Current Market Dynamics: Consider other factors like inventory levels, the competitiveness of the market, and personal circumstances.

A friend and I have an LLC that owns multiple properties and for several reasons we would like to split the LLC into 2 LLC’s and each own one. We would like to split the homes and both have separate LLC’s moving forwa...

That's the important distinction though. 

@Saji Ijiyemi There could be extenuating circumstances.

A simple one page option saying. 1) I understand because of your circumstances you’d like to lease  MTM.2) I don’t usually do MTM leases and it’s harder to lease my property in the “winter”3) because you’ve been such good tenants I’d be willing to make an exception for you at the rate of $x+$200 with the stipulation your provide more at least a 31 day notice to give me time to find a new tenant.

You should not, under any circumstances, try to flip a house based on what you said above.

LOL.It was probably the best ROI I could get under the circumstances.  

I tend to agree that often it doesn't make sense to hold an already tax-advantaged asset class within a retirement account, however I wouldn't call it stupid.What makes sense is going to depend on the person's facts, circumstances, and goals.