They restricted short-term rentals to one guest per month, then they said only one guest every 90 days.

Grab a cup of coffee and do a deep dive.https://www.stlouis-mo.gov/nst/documents/inforent.cfmI would also check to see if you are in an HOA and if they have any restrictions. 

As a former attorney, you know there are restrictions that apply to marketing for attorneys engaged in other businesses, however, there is a decent amount organic growth that would occur. 

Odds are there is much more hidden here than is being shared.A seasoned investor could probably mitigate these risks, but they would run EVERYTHING to ground. 

3) Is rent by the room a feasible strategy with these county/city living restrictions?

We often use VS for apartments that have floor plans that are a bit odd and find they are very helpful.

The Buyer agrees to use commercially reasonable efforts to secure such financing within [Number] days following the execution of the PSA.Closing DateThe closing of the transaction (the "Closing") shall occur on or before [Proposed Closing Date], or such other date as may be mutually agreed upon by the parties in writing, subject to the satisfaction of all conditions precedent set forth in the PSA.Condition of TitleThe Seller shall convey to the Buyer good and marketable fee simple title to the Property by warranty deed, free and clear of all liens, encumbrances, leases, tenancies, easements, restrictions, and other exceptions to title, except as may be expressly approved by the Buyer in writing.Property DocumentationThe Seller shall deliver to the Buyer, within [Number] days of the execution of the PSA, all documents and information relating to the Property in the Seller's possession or control, including but not limited to, title reports, surveys, environmental reports, leases, service contracts, permits, and warranties.Non-Binding NatureThis LOI is intended solely as an expression of the mutual intent of the parties with respect to the proposed transaction and does not constitute a binding agreement, except with respect to Section 9 below.

Odds are you would receive an automatically generated Notice and need to respond and explain you didn’t file past returns and ask for mercy.

I definitely could've tried to maximize my monthly income by renting the property by room, but with HOA restrictions and my inability to comfortably find a property manager that manages rentals by the room were my biggest reasons to rent out the entire property under one lease. 

Must we forget the other federal agency, the Federal Reserve, is in a highly restricting posture right now, holding interest rates at historic levels to slow inflation.