If I wanted to obtain a loan based on the property's ARV value I would have to wait 6 months. 

Does anyone know if him moving the property to another entity (in any way) would give him potentially more leverage in obtaining a settlement or a modification from the bank?    

A few months ago when I was applying to a lender,  I was able to get a "payoff statement" that doesn't show the status of the loan but the hml made it very hard to obtain and it has now expired so I am very hesitant to ask for another one. 

I have a borrower (self-employed) who is purchasing a 640k property in Orlando area who has had to clear up unexpected conditions in order to obtain a loan commitment, but he has done what was needed and we're back on track.However, we need a few days closing extension and the Listing Agent is difficult, likely because from what I hear, she has a buyer ready and she would get the entire 6% Points real estate commission.I'm trying to be nice, but the listing agent and her title agent refuse to surrender the seller's contact info. 

Depending on the areas, I'm willing to budge on the cap rates that I try to maintain, or the financing I try to obtain.

What are the first skills one should obtain to get started?

In the case of the latter you need an actual landscaping license which is a total unreasonable pain in the butt to obtain.

Just a few comments, not an essay, LOLRestraining a property owner from obtaining equity, such as doing a first and not allowing a second behind them can be illegal, (State laws vary) and is predatory, even in commercial.

I am interested in buy and hold investments with small cash flows with the ultimate goal of being able to pay all of my monthly expenses with the rental cash flow in 15 years and continue working my full time job.Currently I am working to obtain my real estate agent license for the purpose of MLS access and the ability to write offers and control transactions.

Then once you have your goal, you need to create a strategy to obtain that goal and the steps it will take to make that happen.Hope this helps, I manage many homes for engineers, my wife is one and as an active airline pilot I deal with them so I am pretty familiar the mindset of one (I think)If you ever want to sit and chat with me and talk about your plan I would be happy to do so if you think it would help.