I look for properties where the owners don't much care and just want money and then I pay cash with quick settlement. 

Being cheap about repairs leaves you with unhappy tenants who will not take good care of the property because you don't.Send a licensed plumber ASAP.

So, cycles happen and we will likely have another down rate cycle in the next few years but it might just be due to another economic issue, so sometimes be careful what you wish for. 

I was wondering if anyone knows which areas/cities are best to buy a house.

I've wondered about some sort of artists'/musicians' retreat space, but not sure about the numbers of that.I would love to hear your ideas!

Have an opportunity to assume a VA loan and wondering if I HAVE to do it in my personal name, or if my entity can assume the loan.

Protecting yourself from any future issues will require a good understanding of the situation your house is in when you buy it.Tl;dr: crime here is relatively low, declining population numbers don't take students into account, properties are cheap, rents are high BUT be careful where you buy.This concludes my TED Talk, ha!

I am wondering if taking such a risk would stretch me really thin or is there a safer approach to take.

Probably depends on the location and part of town if neighbors care or notice. 

This is not a legitimate business or lender.Be careful and happy investing!