Keeping each LLC’s financials distinct helps prevent this risk.Insurance: Having adequate insurance coverage for each property and ensuring it aligns with the LLC structure can also be a vital component of risk management.Legal Counsel: Regularly consult with your real estate attorney to ensure your structure and practices align with your protective strategy.In conclusion, while running everything through your holding company might simplify bookkeeping initially, consider long-term implications and ensure you are safeguarding each property and your overall investment effectively.

I'm an investor and agent for investors while also having a regular job but I think the answer can often be the same for someone full time investing and "part time" investing.

I didn't say anything about him not moving in and for that year I struggled to cover the regular bills myself causing late mortgage payments and other things.

I assume you’re simply trying to get a regular investor loan in your own name for 50% of the value to pay off the other heir?

Lets face it, the regular buyer/seller aren't that sophisticated, so somebody has to 'lead them around by the nose'. 

Also know that if you hold your property for less than a year, it's regular income taxes on your profits.  

If for some reason you need to rely on regular adverse possession instead of tax sale short statute of limitations, it requires ten years of possession after color of title.

I was talking to an investor who told me if he bought my property, he would borrow money from a hard money lender for a few months and then refinance with a regular lender. 

Her response was that if it was a student I could only get insurance from one specific insurer that is the state insurance (FL) and they are just as or more expensive as other regular insurers.

There are three or four lawyers in Hamilton County that have a regular eviction docket.