I was single at the time, so that made it a lot easier. 

@Chris Volgenau I'm pretty positive Cape Canaveral has had their restrictions in place for quite some time.

Ideally something that is on web/app that'll allow me to keep track of different items come tax time. 

I am currently a full time Police Officer and will be eligible for retirement in four years.

You will have more wear-and-tear, simply because someone is occupying the house all of the time.

7 or 8 times our investment.

Open to any advice from the experts on how to increase traffic as the house would be a great investment for a first-time buyer or to add to a rental portfolio! 

If you have owned it for 5 years and lived in it for 2 out of the 5 years prior to selling it then you will get a proration of the gain tax free for the period of time you lived in it. 

Related to what @Rick Pozos indicated, you need to get a time of death (TOD) appraisal.  

In MN it's $165 one time - no annual fee