And if this represented my total portfolio, it would be like starting over.  

How should I phrase my interest in the property to avoid coming across as pushy or insensitive?

Pensacola is a great market for investing and the number of properties available right now is up so there are actually some on market properties with potential. 

When I have a situation like this, I give them a written notice to accept the property in its current condition or get out.

I've personally done just about every rehab scenario, properties I've lived in, properties bought as investments and even properties bought at auction.You've gotten good advice from folks on this list.

Why hasn't your property manager already answered this question?

For several reasons (property taxes, politics), I would prefer to begin real estate investing somewhere other than locally. 

While it might feel like an extra charge to tenants, these packages often provide value that indirectly benefits the property owner as well—like reduced maintenance calls or ensuring the property is better protected.In my experience managing a large portfolio of properties, these fees are becoming more common due to the thin margins in property management.

There are other loans that do allow you to own the property in an LLC, but you would need to refinance to get into them.

The tenant wants to stay another 2 years.My other adult properties have often had long-term tenants.