You do not need a LLC for every property unless they are large multifamily assets in different locationsFor example worked with a company that had 5 buildings and 1300 units under one LLC.

Because, in that case it is more likely a liability than an asset to you.

I think your plan of buying a second home in your market and renting the first, and building equity over five years is a great idea.If you want to see some 'case studies' of available investment properties (with financial analysis)  in the KC metro, as well as some additional info and stats, I am happy to discuss with you. reach out anytime.

Your time and energy are your most valuable assets. 

A lawyer will likely want you to split them up to protect assets, but more so to make some money making entities. 

Also, think about hiring a property manager.Regarding the Florida ADU,Using a HELOC can be an option, but speak with a financial advisor to ensure it aligns with your financial goals and risk tolerance.

I think Larger deals still may have some juice left to squeeze, but i think This asset class is next in term of correction as we see in crypto, public equities, and debt investing.  

Despite the property's substantial equity, the rising costs have put me in a challenging financial situation, as my monthly expenses now exceed the rental income.

Paying down your mortgage and owning an asset that will appreciate over the long term.If you are paying close to what you pay in rent to cover PITI and expenses then owning a house is a much better financial decision than renting.

For real estate investors, the WeWork saga underscores the importance of grounding investment strategies in realistic financial models and market demand.