Keep in mind the LTV will be <=70%. 

While not the most efficient, I can effectively keep track of approx 30 active loans and it works for me. 

Keep your contractor in check and get an itemized quote prior to hiring.

Learned how to dig deep and just keep pushing forward till the job is done Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Keep in mind that there's no one-size-fits-all answer, and it's okay to take the time to figure out what's best for you.

I keep an eye on the forecast and warn guests about inbound weather, even offering that they can come a day early if the house is available. 

I figured out a system to keep in touch with prior clients (google this for ideas), and lead with a desire to help others...In your post you didn't mention if you have a spouse, or are living with family. 

Most people don't keep good books anyway.

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

Here is a good overview of Sarasota & Manatee, keep in mind North Port has no rental restrictions at all and the city of Sarasota is 1-week minimum, if you are Zoned RMF on the barrier islands STR use is allowed, lastly I would check out GulfPort by St.