I treat them well so they will stay forever and pay off my mortgages.

The effect of this is the account is treated as distributing all its assets to the IRA owner at their fair market values on the first day of the year.

You don’t get to treat people this way and get away with it.  

I believe he is right, that if I do rentals the way HE did it, it may not work out, but I am searching for someone who can help guide me to treat rentals as an investment.

Treat people like people.I purchased a seven unit building in Chicago that was filled with legacy tenants paying crazy cheap rents.

It increases complexity of bookkeeping and is much more challenging to defend in an IRS audit, but it is legally possible.In your specific situation, it appears quite likely that your property might be treated as non-dealer and use the capital gain treatment.

In your opinion how much would be an average standard rate for each unit (treated as condo) in a four-plex assuming HoA pays for exterior, roof, foundation etc?

A state where tenent's get treated like gold and the big bad landlord can bear the cost or foreclose ☠️Around here you often hear of stories about "professional tenants" and for those of you that might not know what that is, it's typically when a tenant shows up, seeming like the perfect fit, soon to find out you won't be collecting more than your first month and security deposit.

Setting up an LLC with two or more investors coming together in the same LLC would be treated as if the party doing the 1031 Exchange is actually buying a membership interest (partnership interest) in the LLC, which would be treated as a partnership for tax purposes. 

@Doran Summers Thanks for inquiring, basically I feel like I been treated as a newbie, where I been ask how much I am willing to pay for closing cost, and several times my lender just send me a loan estimates just to sign without discussing interest rate, points charged, not giving me any options other than just signed the one.