For example, you can have a large capex event like $20k roof replacement, but you can’t necessarily deduct it in a single year.

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The warrantability will come up more on the back end when it comes to refinancing or selling and the rehab aspect will impact you more immediately as it may cause you to adjust some of the work that you're looking to do on the property.

I figured I would still have to be very involved in this aspect, especially doing more than one rehab project at once. 

The con is obviously the cost because in addition to waiting a long time for permit, it requires serious structural changes + roofing, etc. 

Of course capex does come into play, but I have a lot of factors on my side including most major components of the property have been replaced already, including roof replaced 2 years ago, water heater replaced 3 years ago, full house was just repiped, septic system is 5 years old, HVAC system replaced in last 7 years, i do not cover appliances with warranty in my rentals, and the tenant I placed in the property is a single dude who works 60 hours a week and just needs a place to sleep.

Roof?

Best advice is to keep exploring aspects of the RE investing world and decide which feels right and best for what you want to pursue.

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 @Nathan Gesner Funny you should say that as that is what we did yesterday ..we actually lowered it to $1685 and it looks like we have a renter  hopefully  ( fingers crossed ).Income verified , credit score etc It’s a bit low for me but we can get the mortgage paid, the heloc payments and the roof payments and still put some cash flow in  reserves each month as we will pencil out a bit.