It's a numbers game so it's not impossible, you'll just have to shift the numbers & resources to your side. 

I would ask to see any of the lease materials so you know all of your obligations and the rent you should be collecting and for how long. 

You can invest in a good or bad two family in RI or Mass equally, but having a a 20 minute vs. 1 hour daily commute, or being able to see family multiple times a week vs once or twice a month can be pretty important.So I would say choose between those areas first, then when you're ready to start analyzing specific properties to see if you want to put offers in on any of them, there are a lot of resources here on Bigger Pockets for learning to analyze properties, such as the rental property buy and hold calculator.I don't do a lot of owner occupied purchases for myself at this point so the Conventional 97 is new to me also (and has only been around since Dec 2014) but it looks like there are many pages comparing it to FHA so I'd recommend just spending the time to research the differences a bit.You'd want to make sure that if you use a mortgage broker s/he is licensed in RI and Mass (if you still haven't decided between the two), and I'd say to make sure when you are comparing the two options that you consider all the monthly costs (e.g., including private mortgage insurance payments in addition to the regular monthly principal/interest payment) and that you consider all the up-front costs.

I hesitate to call the current market a bubble - there's just too much up in the air to really see what's what, and while RE is a big part of the general health and status of the economy, there are a number of other factors that determine what / when / how the correction happens.The bigger they are, the harder they fall, so unless we (collectively as a society) really have our crap together (which we don't), when we eventually do go down I think it's gonna be a doozy. 

I found this FAQ helpful for research purposes on basic questions I had:https://www.trustetc.com/resources/education/faqs

I currently have a roommate and collecting some rental income (also looking for possible guidance on shielding it from taxes) and looking to rent out the other spare bedroom for more rental income.

BiggerPockets has provided me with such value through its podcasts, articles and resources and I just want to do the same for others. 

There are a lot of good resources (mainly from real estate brokerages).

Thanks for all your insight and resources. 

If the landlord gave you documents (including the estoppel) than you may be able to do something if this what you find when you officially start collecting.