It also can get challenging to set a price now to possibly buy in the future that the owner and you will feel is fair (with markets still appreciating at a healthy pace).You can also keep your eyes open for a seller willing and able to do a land contract with you (but there usually would want much more money down and likely want a full pay off in a few years, but can see what you can negotiate on terms).I agree nothing illegal about options/option fees in WI to my knowledge, but generally seem much less frequently used in single residential transactions than commercial transactions where due diligence and closing timelines may be very drawn out.

Many companies in FL are not writing homes with roofs that are older than a certain number of years. 

He's a young fella and while he won't be ready to buy anything in the immediate future, he will want to be out of this deal at some point so he can free up his credit, etc...

This is my first deal and first time using a hard money lender so I was not aware this needed to be in writing.

You should use a local hard money lender/RE Broker to help you with the loan origination.

One advantage you'll have over people doing a regular FHA purchase loan (non 203k FHA rehab loan) is that when you go towards purchasing a 3-4 unit property and have to deal with " FHA Self Sufficiency," Rule you'll be able to use future market rents that are appraised on with after repair rents (way higher than your acquisition rents probably).This makes it easier to make your FHA loan qualify especially if you buy a good deal that has big rental income upside (your proforma future rents are way higher than your acquisition entry rents).FHA SS rule is required to qualify a FHA loan when its a 3-4 unit property, this doesnt apply to 1-2 unit FHA loans.Even on 203k FHA loans you'll need to meet FHA SS rules (3-4 unit applies to).

I'm a newbie in the RE investing world, but I've been working in the world of property tax for 17 years.

wholesaling is labor intensive, and getting your RE license won't help you invest. 

Even if they do, you need to consider the potential risk that your HOA votes to ban STRs in the future, which is definitely a possibility.I agree with Victor that you should put that money towards a house hack or some other rental property. 

We are currently waiting to see the experience with the Florida LLC, re insurance, tax, beneficial ownership issues before we deed the Virginia properties into the LLC.