Personally, I would be careful in Florida.

The politicians don’t really care the negative outcomes and just want the votes.

Care to share?

Find them at local real estate meetups, but be careful, it's a sketchy business overall.

Security deposit will take care of the last month of unpaid rent, but I'm considering filing a small claims court lawsuit to get a judgement for recoverable damages.

Their system will kick out info, so be careful and verify what you see on there. 

I also don’t like renting really nicely rehabbed properties, most renters don’t take care of properties as well as we would hope.

I want to purchase an investment condo for $150,000.I want to get Heloc loan from my other investment condo for $50,000 and use it as downtown payment for this condo.Can I get a 30 year fixed conventional loan for $100,000 and use $50,000 for down payment from heloc?

I can put 20% down; the rest could be HELOC or a conventional loan. 

I think every market and every person have their own reasons, but here are some thoughts from a property manager.Pros for self managing / cons of PM- Keep all the revenue- You have 100% control- You own listing, photos, etc- Nobody will ever care about your investment as much as you do.Cons for self managing/ Pros for property management- This is a 24h / 7days a week business and I imagine you have at least somewhat of a life I imagine.