It's ok to speculate and leverage but if you believe in the famous BB postulate of "perpetual appreciation" combined with no exit strategy and leverage then your going to be in for a rude awakening, the only question is when.

., it is technically perpetually leased, meaning at the end of the year lease it will transition into a month-to-month lease for the life of the tenant (as long as the tenant continues to pay rent and at the increased rental rate).

This may seem stereotyping, but many of the people you will get from that kind of ad are unemployed.

One of the ideas perpetuated by many of the Real Estate Investment "gurus" is that once you buy a rental property, you continue to hold on to it.

This is because the investor was never really in a position to actually work the asset and assumed there is always a perpetual upside bidder behind them.

Honestly, ive had tenants that were perpetually late in the past.

Stereotypes stifle social change and help to maintain existing systems of inequality.     

Will venture capitalists settle for a fair return, or will they be expecting to buy a percentage of my company's income into perpetuity? 

I do see your point, that it may be cleaner to have the vendor cut the cheque directly to the contractor and still have us schedule and oversee the repair, but there is no fraud being perpetuated.

You could require an additional deposit that would be returned if they stay more than 2-3yrs depending on your preference.Also in my state, if you sign a 3+ year lease its considered a "perpetual lease" and needs notarized to be valid.Overall, it's usually easier to stick to 1 year leases to mitigate risk.