Looks like nothing comes into play until next year but the articles I've read are not clear on when the new rules will be implemented. 

According to the IRS rules you are considered to be disqualified person to your IRA and as such are prohibited from providing any services to your IRA:https://www.irs.gov/retirement-plans/plan-particip...If you had a long term tenant you probably could get away without using third party property manager, however vacation rental will have high turnover, which will require significant involvement from you, and would be considered as you providing service to your IRA, which is prohibited. 

There no reason to wait any time or have any “whichever is lower” rule come into play.

You get zero collateral in the equities markets.Either way you invest, just be sure that you have 'risk management' rules set up to protect yourself. 

There are cancellation of debt rules but we won’t go there because I assume you won’t default on your loan.

Starting 10/29/18 the new rules take effect where you can do home possible conventional 5% down on 2-4 units while already owning other property.

Did you ask your CPA what the rules are for qualifying as a real estate professional?

You now have near or absolute control of the association and can implement rules / regulations that improve the property / community.

I'm new to this as well but the only way I get deals like this anywhere near 12% cash on cash is if I apply the 70% rule to the purchase price.ARV (after repair value) x .7 - cost of repairs = max offer price.You should be paying closer to $100K for the cash flow to be right.J

The conventional financing rules have been 20% down on mortgages 1-6 and 25% down on properties 7, 8, 9 and 10.