We are not in a place financially where we feel comfortable investing (yet).

Then I would factor in which property is more comfortable to live in (do I like the unit you come home to). 

Go to as many groups as you feel comfortable with.

I'm comfortable with anything from a single family up to a 4 unit, hopefully in the Southern Berkshire County area.

We have asked the tenants if they would like to buy the house but they don't have the money for a down payment and having just had their 2nd child they are starting to outgrow the house. 

My day job suffered during those 3 months and now I have a wife that's 8 months pregnant with our first child.  

No  way I could be comfortable with doing that, I've had way too many people who've sounded good over the phone and turned out to be atrocious once I started digging into the background.

I'm in the city so I don't know too too much about them but my suggestion is if they are common in your area you probably want to learn about them and get comfortable with them.

Other than that, if you are comfortable at night sleeping with those numbers...

The website thing might deter some elderly folks who do not feel comfortable using a computer.