At that point, is it prudent to try and repeat this process with a second property?

•repeat/unless I decide To go another route at this pointAny big flaws to this plan?

Otherwise you will be doomed to repeat it and you will never be what is in your heart - to be truly successful.  

I talked to a few different lawyers and I have gotten conflicting information, but most of them said that the medicaid for the mother will not be affected by the life use. 

Ideally, you buy the right property at the right price so u can put your money in, pull it back out, then repeat.

As this is early in the buying process I haven't gotten any quotes to do the work yet so I can't speak to how much it would affect the returns.

Just learn from it and try not to repeat it.  

@Jonathan Tran YES, YES the order here will absolutely affect what could happen on the others.

A lot of my friends who went to college repeatedly changed their majors and overspent by going straight to a university.

I would like to acquire the next 3-4 properties using owner occupied financing where I will live at the property for 1 year, then convert it into a full rental, and buy another property to live in, and repeat that a few times.