@Dylan Grieve - Thanks for sharing, even if it's painful.

So, build as many relations as possible and understand the pain points of sellers.Conclusively, we should widen our market when we have dived in deep into the current one first and have developed some quality relations!

I use Apartments.com for payments and it's kind of a pain (especially when a tenant gives you an incorrect e-mail address - long story) but they don't charge for ACH payments which is nice (though it takes almost a week to process). 

We will keep an eye on the multi-family inventory in MA going forward since if we see a sharp increase in inventory this will be a good forward looking indicator that prices may start to come down.

Paying a bunch of lender/ closing fees twice It’s one of the pains of the BRRRR process

The resident that know all of the rules of the leasing game, what you as an Owner can and can't do, and actively seek to be a pain in the rear.

Your plan is short term pain for long term gain. 

I’m also looking into starting the process to get a real estate license and would like to discuss some of the pain points, general insights, and just some overall advice for that process.Thank you in advance for your time and can’t wait to connect.

As recommended earlier, @Russell Brazil is extremely skilled in both real estate as well in the investment side, do have a convo with him.I'm from Arlington, ended up buying in Reston, then eventually moved to Florida....I likely cannot afford to move back to Arlington (certainly not to the neighborhood in which my grandparents lived), so I feel your pain.

For contractors, it's a pain because they don't get paid until work is done.