@Remy Bonser It's certainly possible, but you need to figure out and understand the different sub markets within Boston you want to tackle and how to evaluate those deals.

I've made contacts with handymen that have made it easier to deal with "minor" issues but tend to tackle the bigger issues myself. 

But then some experienced buyers are willing to tackle it because the purchase price will usually be slashed in order for the current owner to be relieved of that burden. 

My Plan is to continue my day job and in my spare time learn more about how to partner with other investors to tackle our own development project.

We tackled the inside and have created a lot of sweat equity.

I completely understand that there will be all types of ways to tackle this and I'm looking forward to seeing what others are doing. 

I'm not sure I'm ready to tackle Clermont as a market to farm, but it would be great to trade some perspective since we're not too far apart in our RE journey.

Lot's to your post but let's tackle it one item at a time...Loans Quoted - I would call these "portfolio" loans. 

But I definitely wanted to really introduce myself to maybe meet some others who have battled addiction and tackled real estate, or possibly others who are trying to build their empire after an unforeseen accident of any kind.

I worked as a Maintenance Tech for Essex Property Trust at The Highlands at Wynhaven apartment complex in Issaquah Washington for 2.5 years to learn how to tackle the problems that arise with rentals on a large scale, but not really knowing what my goals or vision was.