I have purchased 5 properties, all to live in.

We currently live in Cape Coral, FL, but we are still considering whether our first investment should be in Florida or out of state.Hey Raul, welcome to BiggerPockets and congrats to you and Lilly for getting ahead of the game and preparing early—educating yourselves before jumping in is one of the best things you can do.

As I feel the are i live in is becoming a hotspot.

If they are planning on the $100,000 equity ini their pocket, you need to clarify early on what your offer is, so you're both not wasting time. 

If owning rental properties is something you want to do in the future, it sounds like when you are ready to make the move from your rental, one of the attributes you should consider when you do buy the home you want to live in, is if it would make sense to convert to a rental when you are ready to move out or if a live-in flip makes sense.

I am thankful that we will have the ability to put a large down-payment down (if needed for the numbers to pencil in).

It really comes down to a relationships and putting the work in. 

It's worth looking in different markets though if the one you are in is currently underperforming.

I spent the better part of this past week analyzing the best - and worst investments I made to see if I could identify any discernible difference in the way I evaluated, analyzed or approached the successful investments vs the less successful ones.Here’s the only difference that came up time and time again (but NOT always) - a large majority of the less successful investments were ones where GOING IN I in some way “stretched” to make the deal happen, i.e., tried to make the deal “fit” my investment criteria.  

What part of 44109 are you in, I know a few contractors familiar with what the city’s approving lately.