Hey @Scott Trench unfortunately real estate losses (active or passive) will not offset portfolio income from stock sale gains. 

Guests can become tenants pretty easily.

I've had a BiggerPockets account for a little while but wasn't active at all in the past.

Hi Jon from Boyertown, PA-You and your fiancé are interested in buying your first short-term rental and wonder profitable areas to purchase with a budget up to $500,000.I would look at places along the west coast of Michigan, Grand Rapids, Kalamazoo, and near Ann Arbor, MI.It is important to understand the local STR regulations in each community and partner with a property management company that can help your navigate that and manage it well for an excellent guest experience.Don't forget to look into bonus depreciation and doing a cost segregation study to increase the tax benefits of ownership and if you "materially participate" in the management of the property per IRS guidelines it can offset active W-2 income which most real estate cannot.To Your Success!

I just have it all in the guest document.I do post some info on the fridge.

If you include a low-maintenance marketing plan into your vacation rental, you’ll attract high-paying guests without constantly grinding to fill your calendar.I’ll get back to that in a minute, but first—let’s talk about your reviews.

You'll have a bigger footprint to add cool design elements and offer more amenities to guests. 

With an STR, it has to be absolutely clean, a guest does not want to find evidence of prior guests at all. 

Does anyone need alternative guest coverage for their short term rental? 

- Guest Insurance – Do you require guests to carry their own insurance, or do you use a service like Safely, Proper Insurance, or another option to cover damages?