. - Ability to leverage their network and experience in real estate. - Private lenders are not just sources of capital but can also be strategic partners who bring value to the table. 3.

Use your superior knowledge, experience and analytical ability to spot something in a property being offered for sale that everyone else has missed.  

From a personal standpoint I target 70% LTV for any investment I have that way gives me ability to sell it if I need too

If you are self-employed with no full-time employees you may wish to consider opening a Solo 401k instead of a self-directed IRA as it has several advantages over an IRA LLC such as much higher contribution limits, direct checkbook control (i.e. no need to have the account at a speciality trust company), ability to take a 401k loan, exclusion from unrelated debt finance income tax with respect to investment in real estate acquired with non-recourse financing, etc.Can I contribute to both a Solo 401k and SDIRA?

All units would be metered so data would be there to bill the tenants (so no ability to question the bill) but landlord would still pay the bill given we can not have 4 main master water meters (can only do 2 x1 master meter + x1 sub meter combinations). 

With the city contemplating expanding the ADU ability to city wide, is there any benefit to doing a rezoning now (assuming successful) before the citywide expansion takes place?

The Chicago Association of Realtors'® specifically state "When you become a Dual Agent, you owe equal fiduciary duties at that point to both parties in the transaction, and you lose the ability to negotiate for, strategize and advise either one."

Alot of unknowns as you don't have the ability to walk the property beforehand, but interesting process, and pretty good deals exist there.While the Trustee Sales are cash purchases, there are many hard money options that can turn over the funds in time for the 24 hour funding required to complete the purchase.If you are interested, let me know and I can go into more detail, as well as make some other suggestions for you to consider. 

One tenant moved out giving me the ability to rehab theirs + raise What was the outcome?

That makes a big difference in the answer to what Charles eloquently referenced regarding confidence in your ability to close.