Thank you all for taking the time to read this and I can't thank the community enough for all the inspiration and confidence your stories and motivation has done for my mentality.

Same mentality, same position at the starting line.

I'm 29 years old and mentally I've been slowly transitioning over to real estate as a full time career.

Without having seen the property and having actual bids for the work it's not possible to give an exact number, though, so if you move forward have an overage budget in mind, prioritize the list of repairs to save up for and re-run your numbers to see how the extra repairs affects your returns on the property.Some of those items can be deferred (A/C in particular, as it's October and you wouldn't close until it's November proper), but items like being able to lock the windows are hopefully easy fixes (you can usually add locks to older windows here) that shouldn't require a replacement.

It's not worth the time, effort or mental energy.

Or are you at a place mentally where you're confident with anything that gets thrown at you?

The seller has mentally committed to selling to you and probably wants to see it through.  

Due to this, I began prioritizing my returned letters to determine if it was worth the time to resend them.

I suggest you really look at and prioritize what you want done because your budget will never satisfy your wish list.  

Just ask a bunch of questions until you got a good mental picture of the property.