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. 

The entire exchange period is only 180 days so the max your money will be tied up is an additional 135 days.And there's another silver lining - depending on how the dates line up your 180 days may not end until 2019. 

For replacement costs on my average deal, HVAC is 3-5K, roof 5-6K, water heater $1K, and foundation can of course vary depending on severity and whether slab or pier and beam as examples.Third, decide if there will be any additions, conversions or demolitions whether adding a bath, converting a room to something else, or removal of walls to open up the space. 

_______ What breeds/weight?

The roof is leaking in additIon room.