M question is how to get over this negativity that everyone seems to possess when it comes to being a landlord. 

Probably the first thing you will think of is adverse possession. 

I took possession on the first of the month and collected rent from the tenants that same day (8 units).  

If he is ever behind, take him to court to get possession so you can file the WRIT if you need to.

Automatic Rejection: Your application will be automatically rejected for any of the following:a) Eviction by a prior landlord in the last 24 months;b) Outstanding debt or unpaid damages to a previous landlord;c) Undisclosed criminal record, felony or misdemeanor;d) Being registered as a sex offender;e) Conviction of possession or distribution of a controlled substance;f) Conviction of spousal abuse or violent crime;g) Currently pending the outcome of a felony or misdemeanor charge;h) Bankruptcy in the past 5 years that has not been discharged/released;i) Invalid social security number;j) Outstanding federal tax lien, the repayment terms for which are not current;k) False information on your application;l) Incomplete application, including applicant signature on all pages of the application and this form;m) Failure to pay the application fee at the time of application submittal.

Not being able to get possession and evicting tenants for breaching the contract.

- Hired a property management company in May 2011 to manage my rental property- Typical management agreement between me and the company, included clauses saying that 1) they would collect a deposit equal to one month's rent, and 2) repairs over $150 needed my approval- They found a tenant (someone who worked at the company, in hindsight this was a red flag)- Settled on a rent of $1300 with a deposit of $1300, this is reflected in a copy of a signed/executed lease agreement that I have in my possession- Tenant took possession July 1, 2011Over the next 5 years, there were a few bumps, but nothing completely egregious, e.g. they tried to make me pay for a carpet cleaning in the middle of the tenancy and I pushed back, they refunded.

App_...Actually, landlords in FL still have the option to sit on their hands and not take possession, and continue to hold the tenant liable.  

Some tenants will stonewall you because of fears they will be forced to leave when a new owner takes possession.

The tenant shall at once surrender possessions of the premises to the landlord, and the landlord may without further notice remove all persons and all property from the premises.