If there are plenty of studios or private single rooms at the same price or cheaper than a shared-space room at your place, you will definitely have a hard time filling up.Are there extended-stay motels in your property's area?

Think big picture.Consider all the benefits of the investment over an extended period of time and get started!

Not sure if this has worked through but a winery that has been long on the market might be suffering from poor practices by the viticulturalist.

Rents have softened, though, and currently experiencing an extended vacancy in one.The advice you're hearing here is sound. 

I plan on doing the following:- Full gut demo - done- Extend third floor to rear of building envelope and raise ceilings.

I responded before to a very similar comment to yours"I love this perspective and totally believe that many people suffer form this.

This resource covers FEDERAL fair housing law, but I think some states (especially tenant friendly ones) may extend protections further and may even eliminate some of the exemptions.

Hold your nerve and don't slash prices unless you're seeing some extended time without bookings.

The result is an even deeper inflation than what we already suffer from.

It helps that we don't allow transactions to pile up throughout the year.Most of our Clients before having us do their books would have to extend every year and some even went multiple years without filing tax returns.