@Hannah Potter Here are the things that many CPAs support their clients with:Understanding tax impact of short-term vs. long-term vs. flip before you buyWhich entity structure is best for goals and investment property typeTax and compliance on LLC or S-CorpHow to transfer property out of personal name into LLC (hard to buy 1st through entity)Ways to optimize taxes throughout the yearHow best to set up accounting to track income and expenses (doing this late is a mess)Feedback on property management systems, accounting systems. systems, etcEstimated payments to avoid penaltiesKnowing when to file and getting things in on timeMaybe a few things I missed, but this is the high-level ….. if you can get answers to the above questions on your own, plan, and file your own taxes then you can avoid the expense of a CPA.

Would love to get seasoned investors' advice on how they would solve this investment/tax challenge: I am about to transfer 300k from a retirement vehicle so that I can use the money to retire early.

They also cap ACH transfers in at $5000/month, so if you're in a high-rent market you might not even be able to accept all your rents from a multi-family property through their system.

Lynnett, how do you transfer your reviews from evolve to your own listing on Homeway/VRBO???

If it's a cash person, we add the fee on top of sales price to allow a slightly lower sales price to save on the transfer taxes.The only time we charge a retainer is for out of state buyers.

I have signed a lease and transferred payment of 1st month's rent and security deposit to the landlord.

The primary challenges would be about the safety of settlement transfer for a physical currency transfer (like gold) and the specificity of timing and valuation of transfer in digital assets. 

Here is a link to the Comptroller's guide to the non-resident withholding, which may have answers to your questions: https://www.marylandtaxes.gov/forms/current_forms/withholdin...If link doesn't work the document is called "MARYLAND'S WITHHOLDING REQUIREMENTS for Sales or Transfers of Real Property and Associated Personal Property by Nonresidents" which you should be able to Google.Good luck.

Transfer taxes, recordation taxes, lenders title insurance, owners title insurance, closing fees, lender fees, appraisal, survey, deed prep, recording fees, insurance, escrow 

Being leveraged for a bit isn't the end of the world - there are usually options available if push comes to shove - 401k loan, personal loan, sell stocks, credit card (then balance transfer continuously until you can pay the balance off) and lastly sell.