For the future you should have a check list of items to refer to. 

Rent collection, tenant communication, template leases, electronic lease signatures, marketing, tax form prep, move-in/move-out forms, automated email reminders, background/credit checks, this list goes on.  

Do you think the restrictive rent control is worth looking to buy in Takoma park if I can find something there?

It’s like moving money from your checking account to your savings account. 

Hey @Brooke Peterson - you can check out Events and Meetups forum via this link - https://www.biggerpockets.com/forums/521

Yes for sure - you should definitely check out hard money loans to assist with the purchase and then "DSCR Loans" for the cash-out refinance (DSCR Loans are made particularly for investors like you - no DTI or W2 considered at all)Published an article last year on BP on this exact topic (BRRRR method financing options) hope it helps!

We are a 2 hour drive away from Lake Harmony. 1) Is it worth hiring a property manager?

If anyone has resources (articles, guides) for analyzing multifamily properties, I'd love to check them out!

I just started my new job a couple months ago so that might be a problem for me as I don’t have 2 years worth of income history.

She has been worth her fee twice over, and has helped me a lot.