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!

Banks can refinance a rental property under an LLC, but it sounds like you would really benefit from investor-specific consulting and lending.

It will familiarize you with the basic terminology and benefits.

Both investments can offer tax benefits, but real estate typically has the edge.

It will familiarize you with the basic terminology and benefits.

.- Cash flow vs. appreciation: If the new property is in a market with strong rent growth, you’ll benefit from increasing NOI over time.- Stock market opportunity cost: If the brokerage account has strong holdings, consider if the return potential justifies cashing out now.Given the current market dynamics and your goals, reallocating your brokerage funds into a multifamily property in Rochester could provide substantial benefits.

@Cole Harris what's the benefit of making the move? 

The benefit is that you can take control of the rental while still allowing them to retrieve their belongings.

I know I'm getting the tax benefits of depreciation, the minimal positive cashflow, and the appreciation on the property, but It's pretty much a long term play of slowly raising rents annually to increase cashflow, which will eventually get basically reset when my loan goes P+I in 10 years.

I think the testimony of many on this web site would indicate there is great financial benefit from taking either of those approaches.