This could be huge, or something like the ADU legislation that came out in 2017 and then revamping in 2020 due to convoluted items that made the building very strict to almost nonexistent.The main reason ADUs are hard to get the best value for now is that the appraisals come in short (depending on the comps in the area of course).

If there is rot and its a more extensive of a job than merely replacing the window that will drive cost as well so you should seek a line item budget from the installers.  

Many buyers, especially first time buyers on low down programs, just don't have the financial capacity to deal with a major item.

Then I would still have to do additional work on kitchen,bathrooms, leak around chimney, garage doors, and other misc items.

We invest in the Indianapolis Indiana market and focus on properties around the $150,000 to $190,000 range that are older homes in good areas that have updated roof, HVAC, plumbing, windows and those type of higher cost items to make sure it has good bones.   

The hard part is figuring out what you can easily delegate but that is true of most businesses (I was good at it when I worked for someone else, but not good at it for my own items but want to improve).  

@Eric Lahoda, is it typical in your market to charge fees for those items separately?

In my state, we have to produce an itemized list of all expenses that came out of the deposit within 30 days of tenant moving out.  

With that said, for someone young and just starting out, needing to figure out all of those items; my go to answer is some form of a house hack.

Also, the biggest ticket item will most likely be the main sewer line disconnected, What was the quote for the repair?