Antoine, Looking to buy and hold.

I'm looking to purchase buy, hold and rent single family and multi-family properties in the Chicagoland (IL) and Milwaukee (WI) areas.  

Generally, you can find a bank willing to loan 70% of ARV OR 90% of hard cost (purchase + rehab, no holdings) which begs the question of... why isn't he doing that?

Gone are the days when you'll have an insurance Broker that holds and value your accountsattentively.I have to remind my agent that my insurance is due if I miss that letter from the insurer then boom itis canceled. 

After paying in additional 10% in Principle.Mortgage will go down to 1290/month.I realize there is a negative cash flow to start, but im thinking the 15k in equity off the bat and highly recommended tenants making rent payments in the 1st month is worth it (no waiting a month or more to find a good tenant.)Main goal is buy and hold.

So, for a flip that sells for $200k, you want to walk with $32k after rehab, agent fees, holding costs, etc.

Looking to covert some of my paper assets into real estate holdings.

Look into foreclosures in your local market that you can BRRR (if you are interested in buy and hold) or flip if that is your goal.

Do you go through and get the money and do a POF and if it's not accepted just hold it (and pay interest??)

In general contributions into an entity do not trigger a taxable event.Doing it prior to sale leaves you open to issues of intent and holding period and the thought that you're somehow hiding gain somewhere in the entity transfer.