However, this option shall not be exercised by Lender if exercise is prohibited by federal law as of the date of this Security Instrument.If Lender exercises this option, Lender shall give Borrower notice of acceleration.

That way expenses will be paid from this account, profits will be reported to it, and each account will receive its proportional share of profit or loss.Since each account is buying membership in an LLC, this removes any doubt that the house was purchased by one account, then sold to the other, which is a prohibited transaction.

The condo association only allows 1 or 2 pets under 20 pounds, which eliminates breeds prohibited by my insurance company.

Would this be considered a prohibited transaction?

Hi Jason, If you are asking about Toms River in particular, the biggest challenge with TR is that short term of less than one month is prohibited by the township on the mainland.

It "would be nice", but it's cost-prohibitive.

@Chris Schlechta & @Dennis TierneyYour IRA lending to a LLC where you are a member would be a prohibited self-dealing transaction. 

St Pete and Clearwater specifically prohibits STR nonetheless there are hundreds/ thousands of them.

You certainly cannot perform the services of a realtor and be compensated.It {may} be possible that you could process the transaction and not be compensated, but there is a likelihood that the IRS could view this as providing services of value to the IRA, which would be a prohibited transaction.  

To give you an idea of the requirements, at least half of the Corporation’s assets would need to be invested in real estate that is directly managed or developed by the Corporation.Following are the similarities and differences between the solo 401k and the self-directed IRA.The Self-Directed IRA and Solo 401k SimilaritiesBoth were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from creditors;Both allow for nondeductible contributions;Both are prohibited from investing in assets listed under I.R.C. 408(m); andNeither may be invested in your own business.