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 ?

I am looking to learn as much as possible and assemble a team so that I can invest out of state in the Connecticut market by the end of this year.Some background on me: I am 25 and currently operate a Social Media Management company where I build my client's Social Media accounts.

As an investor you want to maximize your returns which is usually putting down enough skin to generate a solid rate of return.

They're now worth about $200K and generate $2000 a month with very little maintenance cost. 

Dallas and Houston look good on a macro economic/demographic level but when you factor in all of the operating expenses, they don't cash flow well.

I know that's how I operate, but its not exactly whats best for me.

The benefit if REPro is being able to deduct losses from operating a rental portfolio - IF such losses do exist and if they are limited by tax law.2.

Ethical reasons alone should steer you away from this practice.Yes their are people who operate like this but I would sure have trouble sleeping at night knowing that my business model included screwing people over.