@Brad Kanouse Using Traditional IRA funds for an investment property typically incurs income tax and a 10% penalty if you’re under 59½, as investment properties don’t qualify for tax exemptions.

If so, there are no transfer taxes due. 

Instead of jumping into an expensive Long Island market with negative cash flow, consider investing in a Texas market like San Antonio, Houston, or DFW suburbs—these areas offer strong rental demand, lower property taxes than NY, and better cash flow potential.

It’s definitely smart to evaluate the tax and cost implications of your funding options.

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!

Mgt, Landscape/Snow, tax, insurance, utility then debt service. 

I would  show you purchase strategies, real estate monetization, rent roll leveraging, portfolio margining and asset protection/deep tax deductions  

I bought it last year and thus far have: 1) Appealed assessed value to bring down taxes, 2) Got better (less expensive) insurance, 2) Rehabbed 3/4 units, and 3) increased rents $300-$400 per unit along the way.

@rick taxed at short term cap gains I intend on keeping till 1 year markYour other questions I’ve answered elsewhere in the thread

Any tax pro who is familiar with REI will be able to help you.