Hi @Tiffany J. For long term buy and hold in Orlando is is tough ask right now. We literally only have a few weeks of inventory, so prices are ridiculous (from what we are used to here). Going into the summer season, I'm expecting it to be even more competitive as once school is out, we typically see a lot more activity.
If you are able to wait (not always) for new construction, you can get some descent properties in some of the areas you mentioned (Groveland, Apopka, Haines City, St. Cloud to name a few) Cash flow will still be tough, but you will get appreciation and peace of mind with all mechanicals etc are new and warranted. Winter Park is too expensive for single family, you might get an older home on the Seminole Co. side for under $300.
Townhome vs single family is a supply issue right now, townhomes have higher HOA costs ,but generally no exterior maintenance, appealing to younger people that may need to have a room mate and don't want to have a yard etc. Single family, just watch the age of the home. You could walk into a ton of capex (roof, a/c, poly plumbing, electrical panel), not to mention updating if you want to maximize rents.
Hope this helps a bit, reach out if you would like to talk thru some scenarios. Good luck!