What are you getting out of it?

Maybe, maybe notYou have to weight the pros / cons along with the risks.Your BP mentions you are 'new to real estate'.You are getting into a new asset class along with a business(I consider a STR more of a business than an investment).How much will you save in taxes?

If you always use a spreadsheet before you look, you will get no reps.

Best of luck as you get started, and happy to connect with you!

I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?

I was looking to get a new degree in financing, accounting etc and knew I was going to be paying a tuition someway or another.

So many of us have a lot more on the plate and get it done.

"If I can convert that garage into an ADU" or "If I can figure out how to get rents higher..." 

As you'd expect these giys are super busy an d you can't get a quote frpm them to save your life unless you said the magic words;  "I'm desparate and will pay 2x the actual costs today for you to take this job".   

Considering it is literally seconds from the highway i would say the location could not get any better