Does anyone have experience transferring a rental property to an LLC from their personal name?  

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

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

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.

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. 

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.

Trying to figure out if I can buy as individual and then transfer the asset to an LLC afterwards.

Ask to see a copy of the lease and look for the length of lease, current rent amount, tenant obligations like paying for utilities and adhering to house rules and look for Landlord obligations like things the landlord may currently being paying for (like trash and water)Make sure to have an assignment of the lease and clear language on the security deposit WITH interest shall be transferred to the new owner at settlement.Consider tenant quality - what’s their payment history looked like, obtain rent receipts or bank statements from the seller to review on-time payment history.

I would like to transfer these to another LLC where I am the sole member.