If this money is important to you stay in your local market - if you have money to burn/take a chance on.... roll the dice

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

If they cant pay 1 month the chances of them catching 2 up is slim to none.Treat section 8 as any other tenant.

@Vaughn Smith I'm still doing my research on the process, but right now everything is on hold because Auctions are suspended at the moment...If by chance you know of a good RE attorney in NJ that may be familiar with sherriff sales, please share his/her info with me if you can..

I believe it leads the listing agents to having a better chance of double ending the deal.So, how do I see that affecting investing? 

the details and conditions of how things will come together may come at a price... again i didnt get a chance to get close to my 2nd until i handed him a check. you know there are people who come out of pocket for mentorship who are very successful and swear by it. 

Chances seem very very slim that a judge will buy the verbal agreement thing, especially for all 4 months.

That said- if you are going to make the jump, it sounds like now is the time, you don't want to take the chance when you have kids, insurance, etc etc, You can always find another $60k job right? 

I narrowed my search to Kansas City, MO as the location in the midwest I would have the best chance of getting the benefits of cash flow and appreciation in comparison to the NY market.

I would also use old school washer and dryer-top loading as there is less chance of problems.