2) Many of these tenants haven't signed an updated lease in years, so would that impede my ability to require them to sign an updated lease that includes utility bills?

Without more information on your personal financial situation or the property, I've reached the limits of my ability to help.  

@Christina Merlo everyone makes great points here, but one I would add is the ability to obtain gap funding through the form of unsecured debt, used for down payment, closing costs, rehab, (or anything really, since it's unsecured).

This gives you the ability to learn exactly what this'll bring in for cash flow without jumping all the way in.Plenty of options.

Even a $500 increase in rent coupled with the $3,000 for the car and you're looking at almost $10,000 in expenditures that you don't have to make and that will inhibit your ability to grow and accomplish your financial goals.I would try to sit on this for a year and see what you can accomplish. 

You claim the tenant is "stringing you along" and Im sure that is true, but you also have the ability to be VERY clear with your communication and approach.

If you create a program to provide funding for renters but you don't have the money to do it then you need to pause your obstruction of an owner's ability to remove a tenant until at least your program is funded because otherwise it's basically a scam.

This, accompanied with their ability to raise fees at will is why buying a condo or in an HOA can always be a risk to an investor.

That and the lack of ability to communicate with potential tenants and a lack of an available PM (the two I called wouldn't manage it) we stayed away.

Your CPA may be right and Yonah wrong, although your CPA seems confused about the idea that you need to have made a lot of improvements to take advantage of this.Since you are a W2 employee (and presumably not a real estate professional), your ability to take advantage of extra depreciation will be limited.