Pros include securing the desired property and strategic planning, while cons involve higher costs, financing challenges, and complexity.

On the other hand, if you’re financially secure, the low-rate loan and potential appreciation make holding more attractive.

But I also understand some people don’t really care about the cash flow as much as the security of not having to worry about a vacancy or whatever.

Securing financing upfront is paramount.

Private lenders or even creating a small syndicate with a group of investors might also be worth exploring, especially since you can point to your uncle’s track record and your own experience managing rentals as a selling point.If timing is tight, you could look into a bridge loan to secure the property while figuring out a more permanent solution.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

Question is: if I have one of these LLC (owned husband and wife, in a non-community property state), but it's a just a passive LLC - such that all it does is owns public securities (ie, our brokerage accounts are titled in the name of the LLC), does the same rule apply?

It's not an effective strategy but a lot of investors believe throwing in high end appliances in itself secures a buyer. 

Ensure you collect a proper security deposit (typically one month's rent in Florida) to cover potential damages.Your plan to increase rent next year makes sense given rising costs (taxes, insurance, and maintenance).

Also, securing financing is no different than site built unless you're dealing with  someone that has no experience originating loans.