I can give you some more specific advice on permitting processes and building. 

Need to keep in mind STR license / permit restrictions when evaluating.  

Many times, if you wish to hold the title in the name of an LLC, you may end up with less favorable terms or even find that it's not allowed.If you do find a loan program that permits taking the title in an LLC, it's essential to consult with your attorney and accountant to understand how to proceed.

According to planning, only 1 and 1/2 story is permitted in this neighborhood.There are some consideration yet to be taken at this point.

Louis]Single-family home building permits serve as a leading indicator of future housing supply trends.

Our project has been pushed out quite a bit, but as far as I can tell all for legitimate reasons with permitting delays and market shifts.

The con is obviously the cost because in addition to waiting a long time for permit, it requires serious structural changes + roofing, etc. 

Client Name: Property Adddress: Current Property Type: Post Rehab Property Type: Level of Finishes: List Structural Changes: Final Bed/Bath Count: Exit Strategy (sell or refinance): PHASE 1: PRE-CONSTRUCTION Original Amount Net Adjustments Adjusted Total Description Drawings $ - $ - $ - Permits $ - $ - $ - Expeditor $ - $ - $ - Alarm/Security $ - $ - $ - Temporary Fencing $ - $ - $ - Portable Toilets $ - $ - $ - Engineering Fees $ - $ - $ - Architectural Fees $ - $ - $ - Utilities $ - $ - $ - TOTAL PRE-CONSTRUCTION $ - $ - $ - PHASE 2: DEMOLITION Original Amount Net Adjustments Adjusted Total Description Interior Demo Exterior Demo Dumpsters TOTAL DEMOLITION $ - $ - $ - PHASE 3: CORE AND SHELL Original Amount Net Adjustments Adjusted Total Description Excavation $ - $ - $ - Foundation $ - $ - $ - Underground Plumbing $ - $ - $ - Drain Tile $ - $ - $ - Sump Pump $ - $ - $ - Steel $ - $ - $ - Floor Joists $ - $ - $ - Subfloor $ - $ - $ - Rough Carpentry $ - $ - $ - Interior Stairs $ - $ - $ - Dormer $ - $ - $ - Roof Masonry Siding Windows Exterior Paint Soffit/Fascia Gutters Landscaping Walkways Exterior Doors $ - $ - $ - Exterior Stairs $ - $ - $ - Porch $ - $ - $ - Deck $ - $ - $ - Driveway $ - $ - $ - Garage TOTAL CORE AND SHELL $ - $ - $ - PHASE 4: HVAC Original Amount Net Adjustments Adjusted Total Description HVAC Rough Furnace Condensing Unit & Lineset $ - $ - $ - HVAC Trim $ - $ - $ - TOTAL HVAC $ - $ - $ - PHASE 5: ELECTRICAL Original Amount Net Adjustments Adjusted Total Description Electrical Rough $ - $ - $ - Electrical Finish & Fixtures Low Voltage TOTAL ELECTRICAL $ - $ - $ - PHASE 6: PLUMBING Original Amount Net Adjustments Adjusted Total Description Water Service Upgrade $ - $ - $ - Sewer $ - $ - $ - Plumbing Rough $ - $ - $ - Water Heater $ - $ - $ - Plumbing Trim & Fixtures $ - $ - $ - TOTAL PLUMBING $ - $ - $ - PHASE 7: DRYWALL AND DOORS Original Amount Net Adjustments Adjusted Total Description Insulation $ - $ - $ - Drywall, Tape, Sand $ - $ - $ - Finish Carpentry (Trim) $ - $ - $ - Interior Doors $ - $ - $ - Interior Paint $ - $ - $ - TOTAL DRYWALL $ - $ - $ - PHASE 8: FLOORS Original Amount Net Adjustments Adjusted Total Description Hardwood Floors $ - $ - $ - Tile Vinyl Carpet $ - $ - $ - TOTAL FLOORS $ - $ - $ - PHASE 9: KITCHEN Original Amount Net Adjustments Adjusted Total Description Cabinets Countertops Backsplash Plumbing Fixtures $ - $ - $ - Light Fixtures Appliances TOTAL KITCHEN $ - $ - $ - PHASE 10: BATHROOMS Original Amount Net Adjustments Adjusted Total Description BATHROOM # 1 Tub $ - $ - $ - Shower Tile Vanity Countertop Plumbing Trim & Fixtures Light Fixtures Glass & Mirrors $ - $ - $ - Bath Accessories $ - $ - $ - TOTAL BATHROOM # 1 $ - $ - $ - BATHROOM # 2 Original Amount Net Adjustments Adjusted Total Description Tub $ - $ - $ - Shower Tile Vanity Countertop Plumbing Trim & Fixtures Light Fixtures $ - $ - $ - Glass & Mirrors $ - $ - $ - Bath Accessories $ - $ - $ - TOTAL BATHROOM # 2 $ - $ - $ - BATHROOM # 3 - Basement Original Amount Net Adjustments Adjusted Total Description Tub $ - $ - $ - Shower $ - $ - $ - Tile $ - $ - $ - Vanity $ - $ - $ - Countertop $ - $ - $ - Plumbing Trim & Fixtures $ - $ - $ - Light Fixtures $ - $ - $ - Glass & Mirrors $ - $ - $ - Bath Accessories $ - $ - $ - TOTAL BATHROOM # 3 $ - $ - $ - **Please add itemization of work for additional kitchens or bathrooms** PHASE 11: OPTIONAL Original Amount Net Adjustments Adjusted Total Description Other $ - $ - $ - Fireplace $ - $ - $ - Final Cleaning Staging Stucco Closets General Contractor Fee $ - $ - $ - Finish Carpentry $ - $ - $ - Underpinning $ - $ - $ - Footers $ - $ - $ - Contingency $ - $ - $ - TOTAL OPTIONAL $ - $ - $ - Total Estimated Cost of Repairs $ - $ - $ -

Make sure your land is zoned for the type of structure you're wanting to build by calling the city/county planning and permits office. 

Infill lots in the city or recreational lots in the rural areas.. either way you need to buy them at deep discount to make this work.