As someone else stated, banks will want to see a couple of years of rent roll typically , so do a solid job of estimating the current rents for those units and what additional CAPEX is required, apply a 50% rule and CAP rate for the area and that’s the value.

The home is 2,300 square feet and has an addition on the back that was not touched. 

So its not a additional amount I have to pay.

With no income...just cost.How many months would it take to recover $60k...which is what you need to do before you show any profit...and before you mention appreciation, you get the same appreciation whether you pay this way or the minimum.At $18k/y cf (after payoff), it will take you over 3 additional years before you start making a profit...that's actually close to 8 years from when you start the early payoff.B - If you put 20% down (about $24k), that was cash, and you had positive cf (on average) for the full term (let's say 20 more years), the cost of this property to you was $24k.If you had $500 positive CF without doing this early payoff, or $6k/year, you would have broken even at the end of year 4...and you would be profiting.Let the tenant buy the house for you. 

Additionally, I would like to finance this deal with conventional financing if possible. 

The cost and additional income is included in calculations.

In addition, both buildings were slapped with fines due to garbage which the property management company not only failed to clean up, but failed to notify me. 

You'll get some additional benefits with a CSS if you replace an item as you'll be able to claim loss deduction, and also your heirs might benefit if they inherit a property with CSS (too bad you have to die for that though).And then there is the question of the value of money now, vs in the future, or the future value of invested tax saving.So, now that I gave you (most of) all the balls, try and juggle them all in the air and see how it goes for you.I can tell you I choose to spend the money and get CSS for two of my SFR rentals.

The attorney/title company may request something additional. 

I live overseas so it has added some complexity and additional time to the process.