LLC's separate your personal assets from your investments and offer you protection from lawsuits related to your property, they can help to establish a more professional image if you plan to expand, and they provide some flexibility on how you are taxed.There are some drawbacks, included fees and administrative work, but it's ultimately best to consider speaking with a CPA to determine the best option for you. 

@Pat Aboukhaled I would ULS (unit lot segment) the primary house and include a clause in the call option that would prevent them acquiring the DADU.

Regarding the condo/townhome situation in Fort Myers vs Bonita Springs, I would say the more important things to focus on would be the association fees charged, what is included in those, and the rental restrictions of the association.

The coastal land is already near built out including Miami.  

. $69k for a 3 unit with gross rents of $2k a month and total expenses of $800 a month which included management and capX.

Do you typically have a separate bank account for each property or do you have one main operating bank account? 

First, the $316K w/study seems a little light, and I would interested to see some more details on what they included in their 5,7,15 year asset classes.

This would include adding another bedroom and making it a full 2 bath.

Alternatively, your sibling might use a 1031 exchange to defer taxes by reinvesting in like-kind properties, though this doesn't directly fund a primary residence.Other ideas include leveraging a HELOC on the rental properties for the down payment, taking out a 401(k) loan, structuring an owner-financed agreement, or a lease-to-own arrangement.

Kansas City has several suburbs with populations over 100,000 including Kansas City, Missouri, Independence, and Lee’s Summit on the Missouri side and Overland Park, Kansas City, Kansas, and Olathe on the Kansas side.