I've been to one real estate conference, which triggered alot of interest.

I understand that, as an individual tax payer, there are considerations for rental properties vs. personal/vacation properties and cases where expenses will not be deductible.

I have purchased several properties from the MLS, wholesalers, and auction sites, but have yet to pull the trigger on one from a Sheriff's Sale. 

The hardest thing right now is that I do not have a team, or group of people I trust in any of the areas that I want to invest in, which is why I have been so hesitant to pull the trigger on a deal.

I have come into some decent money and I'm feeling like I'm going to pull the trigger in the next month or 2 when I find the right deal.

I will definitely take all these things into consideration when understanding my goal and investing.  

Not complicated, but to be honest, I find that a lot of flippers use sub par listing agents to try and save a few bucks, but end up costing themselves more in the long run by having to hold the property considerably longer.

You should also take vacancy into consideration - every day you don't have a tenant in there is money out of your own pocket.

Haha agreed and will definitely take that into consideration for future tenants.

Frederick is a considerably less risky play than Hagerstown.