@Caryn FischerI agree with Jaron, you should definitely have a consultation with your tax accountant and/or financial planner before you do anything. 

Nothing like word of mouth referrals.Either way you definitely want a way to check/verify their work before hiring them.

The only “good news” is you’re paying for last year’s shortage and thsi year’s taxes, or this year’s shortage and next year’s escrow account. 

Theres someone living in the side that I will be occupying until the 1st of February, but since I JUST became the owner, would it make sense to reach out and ask them something like "Hey its __ the new owner, just checking in to see how you're doing.

I dont have enough properties for rent redi to make sense yet but worth a shot to check out. 

Have you checked the BizBuySell website?

It should cash flow 400/month after taking taxes/HOA into account.

I have some of the required funds in a HYSA, but will most likely need to draw from another account and I'm curious which method is the most efficient in terms of taxes/capital gains, penalties, loan repayments, etc.Based on my previous transactions in the market, I estimate ~$45k cash to close: $20k for the down payment, $15k for closing costs and prepaids, and $10k of starting reserves.

Wage garnishment , attach any bank accounts , and or vehicles 

. - PM provides a cash based accounting report every month, for every unit under management, that clearly labels all rent, all expenses, including management fees, and the net directly ties to the amount of money deposited into my bank account.- PM is a licensed handyman, or has them on staff, and takes care of most unit turn work at a reasonable rate. - PM has no breakup/termination fee- PM does not take project management fees, except on large or complicated CapEx projects exceeding $5,000.