Plus he owns an insurance agency so he really understands how to protect clients from both a legal and liability standpoint. 

In Chicago, it is important to understand the housing laws to protect tenants. 

We had a termite inspection done last week and while there were no signs found of "active termites", we certainly want to make sure we have protection moving forward so will need to get a termite warranty/bond, which is likely in the range of $600-$1,000.

Not only will it be harder to identify expenses you could have deducted, but it will also make it more likely that you get audited by the IRS.Protects your liability -- If you’ve registered as an LLC or corporation in order to limit your personal liability, your personal assets are generally protected if anyone tries to come after your business.

Get a RE attorney to make sure you are protected in the contract and no matter what the seller says about the upkeep, do ALL inspections and do not give anything away because you think they like you and you like them.

I hear it helps protect personal assets, but they can be pricey as well.

Relying on a PM to protect your investment is just too risky in my opinion. 

That type of coverage will almost certainly protect you from almost any type of lawsuit. 

I want to receive the tax benefits and protect myself legally and financially.

Initial tenants were all students, so I used a co-signer agreement for parents to protect against non-payment.