I would greatly appreciate your input on this matter.Here is my setupPurchased property under a TrustLLC in FL owns the TrustHolding company LLC in WY owns LLC in FLI purchased the property sub-to, took over the seller's mortgage and I’m working on setting up insurance for the property.I understand I need to keep the seller as additionally insured in my insurance, but the seller no longer has "interest" (ownership) either in the Trust, nor any of the LLCs nor in the Deed nor Settlement Statement.

Below is my understanding but recommend confirming all of this with an attorney.Lease Terms and Updates: In Wisconsin, you can add clauses to the lease that spell out cleanliness expectations or even include a cleaning service if needed.

This will give you a really good understanding of what you are paying.Lastly, look at the capEx on the property.

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

-Josh    I don't think this is a real estate question....You want to know if he will lose his disability income, if I'm understanding correctly? 

I suggest you understand the 50% rule.  

Competitive analysis is key—understanding your local market, pricing, and what amenities and features guests value will set you up for success.

Experienced lenders understand the numbers and would only rock with a nice spread, giving them room to recoup their funds.

With the cash flow number and the potential equity gain every year you can calculate your estimated return on equity - my hunch is that with $500k in equity it will not be great return.Another thing to keep in mind is that if you have lived in the current house for at least 2 of the last 5 years and it has appreciated a lot while you have owned it then you can sell with little to no capital gains (there is a limit that you may be pushing with that much equity).For those reasons I would probably consider options that involve selling.

The beauty about real estate investing is that theres almost endless possibilities you just have to network with the right people and understand the risk of each deal.