It is what is left after snow removal, cutting the grass, utilities, tenant issues, parking lot issues, property taxes, mortgage payment, etc. that make a difference.

Tenant is now saying that she’s in a hotel because the issue is getting worse and that the apt has had roaches for “years”. 

What issues would there be if I put MY NC house in the LLC that has his name and my name on it?

Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

I can only think of 2 times inn the last decade my client has had to go though an eviction and both times it started cause the owner and tenant had personal issues. 

We don't have any issue getting it booked up for the season.

Quote from @Jim Stanley: You should reserve insurance for large claims.Contact the city and report the issue to them.

Better than underground homes which have issues with moisture etc.

The challenge with S8 in this scenario is you always have a piano over your head and all a tenant has to do is call the code office to create an issue for you. 

Later on, if you decide to open a business account, you can typically switch the account for your loan payments without any issues.