@Kelly DeWinter  I know first-hand that the City of Annapolis requires unit to pass rental inspection to rent any unit in Annapolis, not just Section 8, and that we were not allowed to deny Section 8 applicant if they met our other established credit/background criteria unless we met certain exemptions, like an owner renting the house out short-term while they are away for several months (Section 8 requires 12-month lease). 

In my area, once utilities are provided to a lot, there is no hookup/installation cost to re-establish service after demo.

It would also be an opportunity for me to learn how this all works as well and establish a good relationship with the real estate investing community in my area.

Once you have a relationship established, you talk numbers.

Well, you can liquidate and invest in Real Estate syndications, start up businesses or established businesses, hard money (still semi-active), NNN lease properties or put your money into stocks, bonds, mutual funds and gold. 

We believe this is a good idea because it allows us to minimize our living expenses, and learn to be landlords while establishing ourselves in a new area. 

Be sure ice/water shield is included, vents are included, and establish a per-sheet price for plywood replacement in case the decking is rotted.

I know there is an established system that makes sense.

Done right it may take at least two years to season the business in terms of business credit/compliance and then you can approach lenders with both a high personal credit score and an established entity so you can jump into the commercial game of 5 units and higher.

It is a gamble.