Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

A local RE professional should be able to provide this information to you as well.In New York, we deal with this scenario frequently and oftentimes it does not make sense to legalize ADUs because the permit process is extremely lengthy, the cost is high (sometimes $150-300K for 1 ADU unit), and the potential increase in property valuable is not worth the risk.If you already have an approved permit/plan and can get your renovation down to $80K, you may want to consider this project if the ARV is say north of $800K.** You should also look into any potential property tax increases associated with this change.

As for vacation spots, easiest way to increase attraction is getting creative with designs, especially with paint and get GOOD photos with professional cameras.

He replied, "I don't know how you keep finding sellers willing to do that".Here is the secret sauce, know and understand the seller's motivation, ask questions, and don't be afraid to ask for the terms you want.It is more common in medium-sized multifamily where it is a business but not large enough to be professionally managed.

After all, you're targeting a specific, high value commercial niche that's usually dominated by well connected professional brokers. 

Care to cite statute or FL case law supporting your claim?

I am thankful and looking for feedback from our professional tax preparers. 

If you can qualify for the short term rental loophole or real estate professional, you can use depreciation via cost segregation to wipe out a large portion of your tax bill.

My professional goal is to become a “sophisticated investor” and I am seeking any sort of Jr.

I recommend a thorough risk management survey, preferably by a third-party professional that is trained to spot problems.