You need to monitor your borrower and your collateral. 

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'. 

This way you can always be aware if these are being paid and monitor these bills . 

It is easy to monitor them remotely, which brings up the 2nd issue.

Backstory:We rent the ADU out regularly via STR or MTR and live in the main house currently and are looking to size up.

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.