We moved here to St Augustine two years ago and would love to know of any investor meet up's in the area that I can go to.

Do deep research to find areas good for investing, with lots of people renting, new jobs, more people moving in, steady money flow, and chances for the place's value to go up.

That's what the requirement is for if you wish to move out and make it a rental too.

Hi, it is homestead until this point because I lived in it but moving out next month and ideally looking to rent it out. 

Wholesale deal, it was extremely fast paced and had to move quickly on securing the HML and acquiring the funds needed to close.

Appreciation is just the cherry on top.The last few years Toledo somewhat caught up with appreciation but I believe we are capped now.It's a slow moving market and always behind the rest of the country.There is just not enough demand/infrastructure growth like in other markets to support continued appreciation.Historical data shows the Toledo market appreciating at the pace of inflation which is nothing to brag about hehe.IMO, it's a cashflow play and you should consider building a larger portfolio because it will be safer.Owning 1-2 properties can be a "hit and a miss" and really not the providers or PM's fault.There is a high likelihood of turnover so it's important to build a larger portfolio.If you experience "drama" on 1 or 2 properties, the other 4-5 are performing and can subsidize any losses incurred on the few that temporarily aren't performing.Wishing you much success

Hopefully your flexibility will allow you to move to the market you select to give you that boots on the ground advantage. 

Yes that is probably a smart move. 

I only recommend selling when you can invest in something else that produces a greater return or move closer to your goals. 

I'll try to make this short and clear, but there are a lot of moving pieces.