Also, any PM recommendations in Orlando would be great.

You can go to a local facebook or nextdoor groups and find recommended cleaners, handymen and repairmen.

I recommend you personally talk with each of your tenants and ask if this has been happening.

I always recommend that you have significant cash before buying as real estate is cash intensive business

There are some markets that will write both together and if affordable, that would the way I would recommend going.   

I saw two recommendations to attend the local REIA.

I recommend you do it yourself, @Helene Zernik.

I'm having a hard time finding any estimating tools for this kind of a project, adding a story and multiple BR/1 BA, and wondered if there were any tools, sites or recommendations any of you have for this kind of a project. 

Whether you’re looking at SFHs, duplexes, or other properties, it’s important to pair on-paper data with boots-on-the-ground knowledge to really get a sense of values.If you’re considering anything serious in Detroit, I’d recommend connecting with someone who knows the market inside and out.

I’m open to any advice, personal experiences, or recommendations for someone at the beginning of their real estate journey!