I currently have a 9-5 job as a Software Developer and I was just looking for a new hobby that may also bring in some supplemental income.

I will also be looking into some umbrella insurance plans as well to supplement. 

There are just too many expenses to be an agent to be able to make it with no experience and no cash cushion or another job to supplement the income.

I'm a complete newbie interested in slowly obtaining long term properties to rent out and supplement my income when I ultimately retire (in around 20 years). 

I had to make a business decision to either continue to supplement it at $750 per month for how many years and HOPE that not only would the rental rate increase, but also the equity. 

Are you looking to invest as a means of supplementing your retirement income? 

I had to supplement the extra $23K but it was worth it to avoid taxes on the first property.$50,000 rentalThis property we purchased for $125K with the remainder of the 1031 Exchange turned into a bigger project than expected.

I wanted MLS access to be able to run accurate comps and supplement my property searches via marketing.I think your last statement may be the way to go.....I don't currently have any realtor friends but maybe I could work out an arrangement with one somehow - off the record.

Maybe try and buy an investment property in area X and rent a place in Staten Island and use the overage from your BAH to supplement the investment property. 

My goal in starting passive income is to supplement my wife's income x2 so she can stop working and then I'll continue to work so we can continue to build.