Im really banking on my reputation in my home town and all the good relationships I have made throughout the year. 

If you're an LLC others choose that instead of an umbrella sometimes depending on risk aversion and assets.- Use a standard real estate lease, follow fair housing laws.

My original plan was to live in the home on days off, and any days that I could work remote, while finding a new job in the area.I spoke with a lender who said that due to my work not being full-time where I choose to buy, it would be hard to get anything under 10% down payment.

If he weren't your spouse, would you choose him for a business partner?  

As a new licensee starting out, regardless of specialty, I would highly recommend choosing a Broker who can offer the best training possible in your preferred niche.

Had lots of applicants to choose from.

I put enough in to get my match and while I haven’t always felt like the return has been great due to the wacky options they have for stocks and funds for us to choose from I do now have a nice amount set aside 7 years later.

What community is the Kissimmee house in, that will also make a difference, there are 7-8 that are top tier for returns due to amenities of the community and reputation, if it's not in one of them, you'll work harder to fill it up and get great rates.

As an investor and agent in the area, I work with some investors who utilize lenders that only look at the asset and your credit score (but not your DTI), while others choose to purchase as a second home loan. 

So rather than being angry or bitter I'm choosing to be accommodating.