My job has me in countless neighborhoods within an hour radius of downtown, so I pass the time by doing mock “driving for dollars” since I drive through neighborhoods checking for jobs anyways.Besides trying to educate myself as much as possible on all things investing and real estate, I’m finding myself trying to prepare my personal life and debt for investing, including getting my spouse to a point of comfort with the idea, while trying to make sure I don’t get stuck in an analysis paralysis either. 

Based on my analysis of the area, and comparable houses, I think we can make at least 26k gross a year. 

Congrats @Ashton Levarek for pulling the trigger and not getting stuck in the analysis paralysis mode.These are all great options to start out for those who want to manage multifamily properties full-time eventually. 

What other tools do you use in your analysis for short-term / vacation rentals?

It's not always easy to walk away from a deal but trust your analysis skills and intuition.

@Russ Eisenberg You could get a free cost/benefit analysis quote to be able to see what your potential tax benefits would be from getting a cost segregation study.

You should share information about the deal itself and what your objective is with this property, because then we could offer feedback as to whether or not it is a good deal.Based on the general tone of your post, I'm going to recommend that you pass on this opportunity and wait until you become a bit more prepared before spending your hard earned money on a property (Maybe my opinion will change if you offer some additional detail on this deal).Analysis paralysis is real. 

Would it make sense to perform the analysis as if I was another tenant and paying market-value rent for the unit I live in?

Although I am already an Investor with one rental property I have owned since 2004, in the panhandle area of Florida, I realize that what I did not do at that time is apply real analysis towards the purchase.

It’s a great read and comes with the House Hacking Deal Analysis Calculator.