I don't think you can compare: (1) The pain of a tenant with a job who's paying the full amount of her/his own rent for an affordable place that's suddenly not affordable at all, to (2) The pain of an unemployed or minimally-employed tenant in a similar place with a housing choice voucher, to (3) the pain of a tenant in a B-class place who's choosing to pay a fair bit more for X, Y, or Z reasons.It's amazing how the poor people who do their level best to play by the rules and pick themselves up by their own bootstraps always get shafted the hardest in America.

@Kathy Henley gives you a good road map for delaying your decision pain free.

@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). 

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.