The best indicators is seeing things like that, talking with the alderman or govt offices like assessor, chamber of commerce and seeing what areas are going through a transformation of sorts.

Immediately after getting an LOI or contract i request the following items....Exhibit BInventory of property tools, supplies and personal propertyExhibit CService contracts including trash, laundry, extermination, lawn service, etc.HVAC and/or boiler reportsExhibit D Property management license (if applicable)Certificate of occupancyExhibit E Certificate of insuranceInsurance claims history for the past 2 yearsExhibit F Commission agreements with the leasing staffCurrent property management contractAny other vendor contractsOther Requested Due Diligence DocumentsLast 2 years of financial operating statementsA year-to-date operating statementLast 6 months of bank statementsUtility deposit registerUtility bills for the last 2 years.Property tax bills for the last 2 yearsIRS Tax returns and addendums for the last 2 years (as relatedto the property only) Articles of IncorporationGood Standing Letter from the Department of RevenueAny licenses in the name of Sathyam EnterprisesRent roll for the property for the last 2 yearsSecurity deposit registerPayroll recordsEach different lease typeWritten property policies such as pets and parkingInformation on all rent concessionsList of any uncompleted maintenance requestsMaintenance and capital improvement history for past 3 yearsLitigation history on the property for the past 5 yearsAny operation manuals for the propertyTitle policySite planArchitectural plansEnvironmental ReportsAny mold inspection reportsAny lead-based paint inspection reportsAny fire system reports or citations

The e-appraisal website put the property's value at $736K, but I doubt that's accurate.My hope is that there is someone in this group - hopefully in Maryland - that has done a similar deal and can offer some suggestions.

Do you use airbnb & vrbo, or any other platform for listing? 

Instead of mailing I tend to e-mail or call them on the phone directly.

You will be prolly buying in a different platform and price range, as to not be in competition with one another.

Rent is on schedule E, brokerage on sch.C and they have different taxable basis. 

Even with LLC, can I still do taxes in 1040 Schedule E?

It's another smart, easy, convenient service through airbnb platform connecting hosts.

Do those numbers get transferred to a schedule E or am I actually paying regular old 1099 self employment tax??