So yes, this is my first time having a contractor leave towards the final stage of a project as other work that I've done are minimal like fence repairs, deck replacements, sink repairs, hvac etc.

Appliance repair person lined up, warranties don't work fast enough for STRs, you need to pay to have an appliance fixed or replaced right away.

Should I replace the entire roof or just try to manage the smaller parts?

I believe my home can benefit from minor renovations in the basement bathroom, new laundry appliances, painting, and replacing railings on the home's exterior.  2. 

It's a bit of a costly repair relative to the price of the fridge - they need to be replaced for around $500.

You will need to disclose to your lender if you cannot find a replacement tenant.Can you DM me the property address?

I recently had a buyers agent tell me (at my house) my heat pump was 20 years old and was at the end of its life and needs replacing . 

I was all ready to get my Certificate of occupancy and they told me I needed a landscaping plan for all the trees  I needed to replace. 2k for that. 

Also, I will assume that your goal is financial freedom.Financial freedom isn't just about replacing your current income.

The cost of an water heater replacement for example is close to the same regardless of price range of rent or property value.