do you think this would attract that type of tenant who is possibly selling drugs or doing other illegal things?

Many agents are attracted to Keller Williams however there are many other great firms in your area.Although I've been a broker for 25 years, I never use to acquire or sell my own properties.You'd do well to decide if you wish to represent retain sellers or work with PRO's like investors and lenders.

https://www.biggerpockets.com/forums/12/topics/232...I have a background in interior design & certificate in Building Construction.

Generally speaking, LLC's are designed to protect your personal assets in the event someone pursues a claim against the business. 

The guesthouse is the original house built in the 1930s and the front house was built in the 1940s, so it wasn't designed to be a duplex. 

but hadnt been touched since...so the stucco has these disgusting seashell designs on it....The kitchen cabinets,although in good shape,are very dated also...and the windows are double glazed,but they are the original windows from the 70's it looks like.we are both low on money and could probably just afford to fix it up to the standard matt wants to.But what I am trying to convince him to do,is to rent the house out for the winter and save the income from rent (we own the house right out so have no mortgage) then come back to it next summer when we have the rental money and money we have saved and using that money,-put siding on the house.

The idea of passive income every month is attractive, while also providing housing for others in terms of value.

I believe in "positive thinking, and that you attract what you think."

In my opinion it appeals more to the MCV crowd though because it is on that side so less attractive to undergrads as it is farther for them from school.

Plus, even if the list price of the duplex in question is fair relative to other GRMs in the area, it would need to cash flow to be an attractive investment.