More points of entry and access ought to result in a more resilient economy, but it can also play the other way - by having so many small operators, each could be loathe to part with his/her money, meaning that the system can freeze up pretty easily because of the lack of well-fortified employers that can absorb economic shock.

You need to work out the operating expenses (OPEX) per unit in your market. 

Setting up an Operating agreement, can this be done online through a template or do I need outside help from an expert?

So we started thinking of ways we could entice residents of the neighborhood to rent rehabbed homes without the fear of not being able to afford rent and the property generates guaranteed rent role without high tenant turnover or encountering high vacancy rates.

So we started thinking of ways we could entice residents of the neighborhood to rent rehabbed homes without the fear of not being able to afford rent and the property generates guaranteed rent role without high tenant turnover or encountering high vacancy rates.

At this point, the only thing that I'm sure of is that I want to invest in a home that will generate income.

With short-term rentals, you are responsible for those things but also things like pool care, lawn care, pest control, electrical, cable, furniture maintenance, dishes/towels/utensils/etc, cleanings, (you see where i'm going with this), essentially you are operating a hotel. 

Recently I have been considering investing in SFH or small multi-family properties in Vermont with the intent to generate a rental income stream. 

Let's say, it costs you 1.5K to get your structures in place (holding LLC or Series-LLC, with or without land trusts, with or without separate operations LLC) and 0.5K per year (for maintaining the LLC properly, bookkeeping, lawyer and CPA, etc.) for a total of 2K.

In terms of living on the income my real estate generates (I have a job but not a very secure or reliable income job), would I be better off staying with the properties paid off or looking for similar good deals and mortgaging them ?