COMPLIANCE WITH LAW: The Tenant(s) agrees that during the term of the Agreement, to promptly comply with any present and future laws, ordinances, orders, rules, regulations, and requirements of the Federal, State, County, City, and Municipal government or any of their departments, bureaus, boards, commissions and officials thereof with respect to the premises, or the use or occupancy thereof, whether said compliance shall be ordered or directed to or against the Tenant(s), the Landlord, or both.

Can she facilitate this transaction under herself or any entity because she’s the sole owner and taxpayer?

While you are the trustee, everything you do should be an arms length transaction that should be benefiting solely the trust and not benefit you.

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Baltimore has some pretty strict requirements for STRs, the most significant being that it must be your Primary Residence (I don't believe we can post links in the forums, but google "Baltimore City Department of Housing & Community Development Short-Term Rentals" and it should be your first organic hit).If you're going to go down that path, make sure that the numbers work as a long term rental once you're ready to move on.

If this is your first investment I would not recommend going through a wholesaler or an off market because like @Lucia Rushton mentioned you will not be properly represented in your transaction. 

Is there a certain department that usually handles those records?

Is it possible to wholesale with a short sale WITHOUT double closing or using transactional funding?

There are several free websites to call about crime rate, but I would first start by calling the non-emergency police department in that area and ask them what kind of calls do they get in the area you are interested in.

@Gabriel Kreider might not be a bad idea to work with an agent just so they can oversee things and make sure the transaction goes smoothly but definitely something you'd need to discuss with the person you're buying the property from as they may ask for a transaction broker fee.