I would install security cameras pointed at the road and entrance.

What about the improvements to the basement, including kitchen, separate entrance etc? 

These are the HOAs that collect ~$100 per year to maintain minimal common areas such as neighborhood entrance landscaping.   

The house has a finished basement with an already sectioned off bedroom, bathroom, living room and a separate entrance from the rest of the house that I can rent out for around $800 per month, while living in the upstairs.

There is no door or evidence of a previous entrance from the inside common hallway.Any suggestions?

Think same entrance, shared kitchen and laundry. 

My Condo has a private entrance, 3 bedroom 2 bath, and allows dogs with NO weight restrictions which is pretty uncommon around here. 

What’s unique is that the basement only has an exterior entrance so if I added rooms to the basement, they would essentially need to walk outside to have access to kitchen/bath/laundry.

I owe 420k on the house (2.2k/mo mortgage) and live in the 4/2.5 upstairs while my renter (medical resident) pays $1375 to live in the MIL suite that is a 1/1 - it has separate entrance/exit.

Separate utilities, four kitchens, four bathrooms, four entrances.