@Sara BlatzMany factors.

I know some things can only be learned with real-world experience and at some point, I will need to take a leap of faith and purchase while venturing outside of my comfort zone.I'm sure this will depend on many factors, but what concepts do you think are critical for a new investor to understand.

I suppose you'll need to factor in what an average fee will look like for the deals you intend to work. 

(we have plenty) Is there any make or break factors for you?

I believe his all-in costs for the reno will be $140,000Below is a zillow appreciation map of the zip code in Columbus.Here are some comps (remember to factor in the appreciation when looking at the closed comps)Follow this link to see the page:https://www.flexmls.com/link.h...This link is valid until 10/29/2020.

You're making this overly complicated.Short-term rentals are complicated as is, and have different tax treatment than traditional, long-term rentals. 

Edit:  My father has specifically stated that his age does not factor into their real estate investment decisions (the idea is that I would do all the work anyway). 

If you can hold it long enough to get capital gains treatment you'll save some tax, or better year, get a Roth and do your flips in the Roth... no tax (but leave the money in).

Many factors to consider like - Can the residents afford an increase, are they great residents, am I getting a decent ROI, do I want to create the risk of turnover, etc. 

The Structural bracing, lateral loads, snow drift, etc. require a higher safety factors.