The listing will always be high but eventually the lenders will come down and in many cases you can get them to 85% and even lower with a good counter BPO (get rehab estimates and good photos to supplement your counter offer)

Typically they will need a supplemental heat type if the weather gets below 35-40 degF for very long (which it will in Maryland).

Having the knowledge as an agent will serve you well as an investor and you can definitely supplement your income.

Ideally I'd like to supplement our contribution toward my daughters' education.

Now, to be an even better investor I would supplement his advice by using modern computer devices to analyze deals.

Here is a list of a few that I find to be of most value:Population TotalHome ValuesHousehold IncomesPoverty RatePopulation AgeRental Vacancy Rate*Homeowner Vacancy Rate*Educational Attainment Rate (High School/GED & Bachelors)Number of Housing UnitRent to Income Ratio*Rent to Price Ratio*Population on SNAPS (supplemental nutrition assistance program) percentageProperty Tax Rate*Median Age of BuildingsNumber of Structures by Units (SFR, Duplex, Triplex, Quadplex, etc...)Median Rents by Number of BedroomsPopulation Change (Births, Deaths, In-Migrations, Immigrants)*note that some of the metrics are composites that are computed by comparing two or more variables from the ACSA number of the variables above can also be broken up into cohorts, which will give you even more insight into how an area is doing.

We are going to be empty nesters in a few years and would like to quit or jobs and move to South America and using the revenue to supplement some of our income.

When we do, we wait to see what kinds of furnishings our tenants will have and then we supplement with furnishings or decorations of our own.

What I'm interested in understanding is how to take over payments or have the owner supplement those payments in a purchase agreement. 

Basically, use the policy to buy other assets, then you can use the policy (if designed properly) to supplement retirement when you're done obtaining assets.