The biggest challenge / drawback of the location is parking. 

i don't have a lavish lifestyle (traveling is my biggest expense and i'm still a bargain shopper at that) and i really don't have to leave an inheritance to anyone since i'm single and no kids. lastly, i can also return to my healthcare job if need be or if i get too bored.

One of my biggest Struggles in todays climate is the fact that when I find a really nicely rehabbed home or flipped deal.

You should target ~30% - 30% expense ratio (expenses/revenue).Also, the pro forma rents they have are most likely higher than what is in place because it's a value add deal and the goal is to Reno and then push rents.I've never used the valuation calculators before, but I would trust my own math in excel more than that.

Adding additional revenue streams such as storage and covered parking.

This is not without issues (the biggest of which is getting more funds into the IRA/LLC after future contributions), but it is worth exploring if it might be a good fit for you.On the other hand, if you are not looking for as much control, I have a great deal of respect for Quest Trust Company and it's owner Quincy Long.  

Typically, if you want to write items off, you also need to recognize the revenue on your taxes (which you legally need to, but many people rent a room to a friend and pocket the cash).  

Before I jump in to this investment property journey, I’m curious to learn how you set up business expenses, rent collection, update costs, etc organized so it’s easy for tax time and analysis.are there programs or sy...

It is the biggest loophole with the most opportunity for raising tax revenue (and impacts the least number of people).

From what I've read and heard, the biggest advantage of BRRRR is creating forced appreciation for when you get it appraised, to pull out more money then you put in.