Preferably one who specializes in investments and works with investors (In most cases its FREE to work with a buyer agent because commission comes from the listing side at least in TN thats how it works) Thats your first step according to @Joshua Dorkin and @Brandon Turner.

More cash out of pocket, more eggs in one basket scenario and slower process to buy a second property, eventually (this includes moving out of my coop with which I have a love/hate relationship)Sell my current coop, buy a duplex with less TLC needed in my preferred neighborhood, move into the property for an unlimited amount of years, qualify for an FHA loan and use the extra cash to continue saving to purchase a second property in 1 year or 2?

As long the rates are competitive they are great because you don't pay origination...and it doesn't show up any place as a liability since it is just a contract between two individuals.

Your taxable income in Year 1 is in the top individual tax bracket, 39.6%.

We haven't talked about the details yet, but I am under the assumption we would both like to do this extension outside of VRBO.He stated that if we are to extend his stay, he would prefer to pay us at the beginning of a month, for each month he will stay going forward, instead of paying one lump sum like he did on VRBO.

Just use an individual name and you will be good. 

I think jay would echo what we practice - unless there's a compelling reason (financing, political stroke, or discount on land) I will always prefer and attempt to buy out the land owner and get them out of the way. 

I would prefer flips and/or rentals, as this is the niche I have decided to follow at this time.

God I wish I had bought some then... had no idea how creative I could have gotten.Just keep rolling the way you are, and you’ll have more deals than you can handle, especially with a good full time job’s income to work with.As always, if you’re unsure of your skill at negotiating, etc, find a good partner you trust, preferably with some good experience, like a (good) realtor or contractor, who have value to add and learn from them.  

I'd prefer to minimize the amount of tuition I pay in the school of hard knocks!