I don't know anything about the Richmond market. 

Booking.com is definitely gaining some market share as of late.

We went to go see a house that is below market value however, the house needs quite some work. 

I see so many articles about the protective benefits of doing this, but my lender (and other lenders I've asked) say that residential mortgages cannot be held under LLCs (only commercial mortgages can), and that doing so can cause your entire loan to be called at once under penalty of foreclosure. 

@Michael KaminskiIf your existing home is on the market the bank could do a traditional bridge loan which is short term and gives you time to sell your home - just want to make sure you have plenty of equity that when it sells it can pay off that loanWhat state you in ?

They are zoning and land use regulations, accessibility, environmental factors, market analysis, topography and terrain, utilities and services, neighbourhood characteristics, restrictions and opportunities, development feasibility, financial analysis etcetera.

We have also started building a base of past guests, where we market discounts during the week (they opted in), and have had a couple bookings from that.

We might sell if the rental market doesn't pan out—so curb appeal is important.  

I don’t think it’s market dependent here is why.

Research local market rates to determine how much more you can charge; often, Airbnb properties can command 20-50% higher than traditional leases, but this varies by location and demand.