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.

Adding the drywall layer will make all your doors and doorways a pain even if you're replacing every window.

I can imagine trying to get through is a pain, I appreciate it 

Refi costs will be $3k + pain and suffering. 

Present a problem, build the problem up to a pain point, and then offer the solution that solves the client's pain.  

I'm not trying to be a pain and trying to state it without looking like a troll(very hard on the internet sometimes), but what I was saying is defining hard money is hard, and being licensed is not 100% necessary depending on location. 

I have had multiple people come to me from BP after dealing with the slow and painful loan processes of MACU.

Appfolio (what we use) is a pain to set up but like you, once it is set up, works great.