I'm looking at a low cost of living area that's plagued with a housing shortage. 

What does it cost a family of 4 to go to Disney for a week?   

I honestly should have more money saved up considering my years of working full-time, however younger financial mistakes have been a painful lesson and I regret not purchasing a property sooner/younger.My most important and immediate goal right now is to purchase a property.I am in (what I perceive to be) a relatively high cost real estate area. 

So many new investors that live in high cost of living areas look to the midwest or other cheap areas to invest. 

This is especially true if the property requires significant upkeep or if the heirs live far away.Owners of Distressed PropertiesSellers who own homes in poor condition and can't afford the necessary repairs may prefer to sell as-is rather than invest time and money into renovations.Landlords with Problematic TenantsLandlords who have been dealing with problematic tenants, frequent vacancies, or costly property damage might want to offload the property quickly to cut their losses and avoid further hassles.Owners Facing Major Life ChangesSignificant life changes, such as health issues, retirement, or downsizing, can motivate people to sell their property quickly.

The cost to join is nominal but well worth it.Other groups to join (if you are an investor and not a GP) are 506 Investor Group and Private Investor Club.

When trying to do the deal analysis on my current property, it’s asking for the purchasing and closing costs.

You will also have closing costs. 

To be honest, your cost to get in a duplex would be right around the cost to get into a SFH in that area.

Negotiated a small price decrease due to it being on the market for 60+days and also had seller pay 3% closing costs.