If by some chance there's profit and the depreciation recap is more than i think then you can do a 1031. 

Chances are, he has a decent client base and is working with quite a few people at the same time.

@Craig CurelopJust got the chance to listen to some great podcasts read one of BP's books.  

And when it comes to specific deals, for example in fundrise many of them are highly leveraged beyond what I'm comfortable with should there be a severe downturn.But, if you're an aggressive investor then you will look at all that in the opposite way.Personally I find a better chance to find more conservative deals on platforms Like Crowd Street, Arbor Crowd etc.

I hope we get the chance to eventually meet up and discuss.

Given how challenging the market is in the greater boston area I am including a lot of towns as I'm looking for the property that has the best chance to cash flow. 

There is almost no chance that you have a problem in the next 20-30 years, but $60/year is almost no money.

or at best barely break even once all expenses, vacancy, and capital expense reserves are taken out. 

But I always have my heart set on escaping this rat race.So I kept working, every chance I got.

What are my chances of winning?