Since Orlando has weather (and an economy, look up 2008-present foreclosure rates in Central Florida for reference) that is very conducive to a large homeless population we have been dealing with the issue at a large scale for a long time, and a lot of caring, smart, experienced people all agree that there are very constructive ways of dealing with homelessness and very destructive ways of dealing with it. Time and time again, allowing the homeless to disperse geographically and survive in a "free for all" state creates enormous problems. You end up with exploitation, abuse, and harm to not only the homeless but those around them.
It's rare, but not unheard of, for stupid kids to give the homeless sandwiches laced with, say, exlax. It's rare, but not unheard of, for people to entice the homeless into essentially handyman jobs with the promise of a meal, or payment, only to "reconsider" at the last second once the job is done. It's rare, but not unheard of, for well meaning people to give out food that has gone bad, or can exacerbate terrible allergies or medical conditions.
Furthermore, encouraging the homeless to beg and subsist off of random passerby is an incredibly demeaning thing. It encourages the bad element of panhandling, begging, and lies to encourage donations. It creates an atmosphere where the most seriously poorly off end up being "out begged" by the devious looking to snag a quick meal, or beer money.
Last, but not least, it completely ruins standardized initiatives to solve the problem. The homeless are less likely to congregate in safe areas where organizations dedicated to help them are located. They're less likely to receive a steady, nutritious diet. They're less likely to be exposed to further job programs and mental health help. They're more likely to sleep in an alley somewhere instead of, at worst, gathering near a shelter, or at best, getting a bed in a shelter where they are safest and most secure. Keeping tabs on the homeless is one of the hardest things to do, but one of the most important. If you can't track progress on a community or individual scale you can't tell whether or not your efforts are working, and you can't develop the personal relationships and support groups that time and time again are proven to be, overwhelmingly, the most effective way to get people out of the vicious cycle.
It's hard to kind of shut off the automatic empathy that pops up, but you have to realize these are people just like you that ended up with a serious short stick in life. You need to treat them like that, instead of infantilizing them.