@Laura Abbott Thanks, I've been in touch with him pretty regularly, but just wanted to see what else people from BP had, if anything. 

Your home owners exemption will only apply to SFR and it will apply to the percentage of the multifamily you occupy. ie: if you live in a 4 plex as owner occupy in one unit then you can claim 25% of that as owner exemption, the other portion you can do a 1031 exchange, so as long as you buy something else you pay zero taxes.

No one informed me and one of the tenants admitted to seeing it at least 4 months ago.My question is can I claim it is not wear and tear and that they are responsible for it?

Update:  I shopped around a lot, and was able to secure 4.00% when my regular lender was robbing me at 4.37%. 

That lawsuit is a claim for fraud, and that’s what fraud typically is...a misunderstanding and someone being “injured” and wanting to hold the other responsible for it.

The other risk is that if you come in and kick over the hornet's nest, one or more of the neighbors could go to land court and claim "adverse possession".NC might be different, but here in MA, if you use the property of another, "openly, continuously and notoriously" for a period of 20 years, you can file an action and potentially own that property.If you really want to remove that road, you need to block it off for at least a day to break the "continuously" element of the test.  

I am planning on getting a regular inspection done, I might need someone to come look at the boiler, and I also want to get the gas/heat metered separately to the tenant. 

When you submit claims, the insurance companies will track that information and it may result in some increased premiums in the future for coverage. 

Need to quit claim deed in my name, make primary residence, outfit entire house with furniture (15k~).

Assuming you (and perhaps a spouse) are the only members of the LLC you may be able to do a quit claim to your personal name for financing.