Most very successful STRs seem to have direct booking options, they are opening their properties to the YouTube Airbnb influencers to get more publicity, they are creating regular content through their own social media channels, etc.  

Proximity to hospitals, corporate hubs, and schools is an important factor.

However, this generic statement is useless for many reasons:- your two years are never identical- even if you expect them to be identical, we don't know the future, and things can change- you likely have a number of special factors that change your tax outcome, some of which I mentioned above and others mentioned in earlier comments on this threadWe are also assuming that you're selling outright for cash and not reinvesting, although you have other options such as installment sales (aka owner financing), reinvesting into REITs/DSTs, opportunity zone funds and more, as mentioned in other comments.Finally, nobody brought up what I consider the single most important factor in your decision process: you sell when you have a good offer, period.

The influencer/incel types.

Key factors include your experience level, credit score (600+), down payment (10-30%), property appraisal and ARV (65-70% of ARV), project scope and budget, exit strategy, cash reserves, market conditions, and lien position.

@Bruce LynnThey could but in reality it’s not the actual federal govt employees that are the biggest factor it’s all the lobbyists and government contractors that flock the area.Every large company has a contingent of people here to grease the pockets of all the politicians

Other factors to consider are what you plans are for the future (value add rehab, restructuring, selling the property soon, etc) and whether or not there are any events on your personal horizon that may impact your ability to refi later. 

When I started, I wanted to leave my small business to pursue multifamily full time, and I did not have the time to fix and flip or buy a few single families scattered around.Those factors led me to start with multifamily.

All of the factors will keep you from cash flowing.

I would argue that the MOST IMPORTANT factor for success will be a boots on the ground team that knows the STR market in and out.