Apparently, Chicago/IL landlord law requires regular payments and/or accounting of interest earned from security deposits, and failure to follow through on that can result in a fine of treble the amount of the security deposit. 

I have a finance background, but I've never structured a RE deal for investors. 

You're definitely walking a fine line when choosing to do it.

;Roth IRA funds are not subject to requirement minimum distributions (RMDs);The fair market value (FMV) of assets held in a self-directed IRA is reported on form 5498;The fair market value of assets held in a solo 401k are reported on Form 5500-EZ;At termination, the solo 401k is required to file a final Form 5500-EZ and 1099-R; andAt termination, the self-directed IRA is only required to file a form 1099-R

If you're feeling generous, go back over and let them know that the tow truck is on the way.The HOA will send a letter to the owner, which would give them 10 days to comply before imposing a fine. 

In a perfect world......But I wouldn't hold your breath and I'd be surprised if there's anything more than sympathy for the criminal, much less punishment or a fine they will never collect anyway. 

For the buildings requirements I just cannot have anyone stay for under a month, and they must abide by all the buildings posted rules or I am charged with a fine and responsible for getting them out.

Hi Christopher,You're idea for question 1 is a fine solution.Regarding toe boards. 

I'm not a finance guy and i don't know your financial situation, but you would probably need close to a 200k yearly income to purchase that on FHA loan and i have not seen too many young families to be able to do that.I'm guessing you are already pre-approved though if you are already working with other realtors.My advice to you would be to be more realistic with what you want and what you can afford and what you should offer to a property you like in order to have a chance to get it.If you had purchased a 400k property 2 years ago, you would already have about 40-60k in appreciation so keep that in mind next time you put an offer on a property. 

@Andrew Dodds, the way I read what Amber and Chris wrote, you could treat your $181k remaining VA entitlement as if it was a HELOC (like having existing equity), which should more than cover the required deposit that you might need for your next $500k home.Of course, your Non-VA Lender will go through your Debt-To-Income Ratio with a fine tooth comb, so depending on how much Rent they allow you to allocate towards your income, you could be good to go!