can't even begin to understand where you are today, but you and your family understand, and that's all that matters! 

While I understand appreciation isn’t something I should necessarily bank on, but I am looking to hold for the long term and eventually relocate to the FL.

But, you need to understand the intensity, time commitment, capital needed, and skill set required.  

Of course the listed price may not be the actual rented price, but by tracking several listings for a while you can gain a better understanding of the market.

For example when someone wants to have financial freedom and spend more time with family, but then sets a goal by creating a heavy active income stream that involves their personal involvement daily.

I’d prefer less outsourcing on behalf of the banks and fewer web portals/ apps/ servicing companies because in my experience the more entities involved the more glitches, so adding a VA and another layer of software to the mix doesn’t sound inviting.

or "No", really don't understand tenant and vacancy management.

Taking real time notes on deficiencies allows for clear understanding if the items make their way to a buyer repair addendum.

I understand the condition of the property may not be great, but if you're just trying to get rid of the property, then why does the condition matter to you?

Any owner who understands STR arbitrage will want a premium.