Ideally I'd be looking for the right property close to home in the North Attleboro, Attleboro, Plainville, Foxboro, Mansfield area.

If you can get the tenant to agree to give notice to move out, ideally in writing, you will not have to worry about the following difficulties as per NJ law.

As a buy and hold guy I am looking for greater security than a wholesaler or flipper might have seeing as they are going to get out of the property, ideally before it floods, and I want to have the home kept nice and safe and dry for a long while.

Repair Estimation/Budgeting - Ability to create detailed Scopes of Work & repair costs budgetsBudget Tracking - Ability to track your actual expenses against your initial budgetScheduling - Ability to create a project plan & track project progressChecklists/To Dos - Ability to track daily to-dos and checklists of items that need to be completedCalendars - Ideally all of your Schedules & To-Dos feed into a Calendar that you can use to manage all of your projects in one location.Document Management - Place to store project documents and photosHere are some Project Management tools that you might consider:Trello/Zoho Projects/Basecamp  - General project management software that includes tasks, Gantt scheduling, calendars, project forums, document storage & team collaboration toolsBuilderTrend / Co-Construct - These tools are built specifically for custom homebuilders/remodelers and have a lot of functionality. 

Ideally I would like to get into Real Estate Investing, doing rental properties and flips.

Fastest way: BRRRRBut the ideal strategy is based on your time commitment and current expertise. 

They like going out to movies, adventure sports, vacations, eating out, etc.

My ideal first investment would be a 2-4 plex. 

It's not always that the worst house in the best neighborhood is the ideal choice.As you mentioned about your market, multiple offers exist above asking within 48 hours of hitting the MLS.

Ideally I'm looking for 2-3 unit houses/buildings in Easton PA to buy and hold... but I'm also open to fix and flip if the deal is right.