I'd recommend looking at similar nearby properties that have sold with 1 or 2 adu's.

Depends on the scope of the project, but I'd guess yes if a more extensive project or your messing with plumbing, electrical, or HVAC.

I could probably do a 3-5% down payment for a property here but the mortgage payment would still be higher than I want to pay as the loan size would be bigger because I’d be buying a $500-600K+ house. 

If this is something you might be interested in, I'd be happy to chat more with you.

I’d like to hear from someone that has first hand knowledge that has done this recently in Florida.  

I'd like to use for future endeavors. 

For these elusive big fish, I'd drive out to the property and talk to whoever's managing it.

Unless you're all in and enthusiastic, I'd just toss money in an index fund.

I'd be happy to recommend their services to others seeking similar investment opportunities in Southeast Iowa.

For your specific situation I’d wait until you get $200k+ saved up and buy better asset classes…even if you have to wait 5 years.