I have thought about that question and my end goal is to build a big enough business where I no longer have to work (outside of real estate, of course) and I can financially support me and my family with income generated from the properties that I'd own. 

I've read conflicting information about what triggers you to have to pay self-employment tax on your short-term rentals.There seems to be a consensus that the following does:Airport TransportationProviding cooked mealsOffering ToursCleaning during the guests' stayDecorating the property for a party as a serviceI'm not sure if these would cause me to have to pay self-employment taxes, as I've seen these items on a couple of lists but not most:Providing a coffee stationProviding a welcome basket with food itemsProviding bikes and kayaks for the guests to useDoes anyone know where the line is of what you can and cannot do and provide?

If they cannot generate income from it they may say "No." 

Usually, the buyer is self-employed and has claimed too much in tax deductions so the bank won't give them a loan. 

This is why we use whole house or stationary gas generators for backup.Natural Gas is best.

and you didn't have the generator fixed or replaced. 

For example, one partner wants to employ a 1031 exchange or another tax strategy and the others just need money as soon as possible.

But I’m not knowledgeable on these sorts of repairs so I may be employing over-caution.

In my limited experience I would say that if you go virtual in a different market (say a smaller city with lower priced homes) you'll generate more leads, but you may struggle with disposition as there is less Investor activity from your potential end buyers (Small,Med, and Large Flippers, Institutional/Hedge Fund Buyers, Turnkey Operators..etc) On the flip side if you stay in the more competitive market it will be a grind to get those first few leads and to secure a contract but your odds of not being able to dispo it should drastically decrease (Assuming you have a discounted deal in the right area) and that check should be NICE. 

One month of income is not reliable when self employed or even for W2.