Based on this some elements of my REI strategy are going to need to be adapted!

I'm from Grand Rapids.I use a 11"x18" graph paper and a daily morning workflow - combined with Google Calendar.

I was in a similar position a few years ago, but fortunately got married and our combined incomes helped us qualify for a larger house hack.We're on our second one in NOVA, Alexandria to be exact, and instead of rent by the room, we are renting out our walkout basement on Airbnb to monthly guests.That said, we have a number of friends doing well with rent by the room across NOVA, though they're purchasing homes with 5+ rooms or finding homes that can be renovated to include that setup.I'd recommend attending meetups such as the one I cohost, NOVA REI or Cashflow Breakfast Club or any of the others to meet those who are house hacking.

I never made more than $100k in a year working until my last year of employment, and still managed to retire at 50 with a lifetime pension from a combination of military and public service.

It is the combination of all cash plus lack of transparency and due diligence allowed to the investor that would worry me.Hope that helps.

The easiest solution to combine your two Stessa accounts would be for you to add the email address you have associated with BiggerPockets as a collaborator to your already active Stessa account.Then log in with your BiggerPockets credentials (as that collaborator) and it should upgrade your Stessa account.Here are some easy steps to follow: https://support.stessa.com/en/articles/2105533-the-power-of-portfolio-collaboratorsIf this does not work, please message [email protected] and we can work with Stessa directly to get you set up.

The combination of high costs and the after-repair value (ARV) frequently leads me to conclude that buying a new rental property is a better use of capital.

I suppose I could combine the two ideas and live in a basement while renting out a 2 bedroom home to a traveling agency. 

@Luke H.Hi Luke,  As a private money lender myself I will focus on one element of your deal---5 years is a long time to be finally paid. 

A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.