It’s has hardwood throughout, fenced yard and screened patio, great school district etc.

Whether I find a new tenant or not, the departing tenant moves out after 30 days and is treated like an ordinary termination, which means I process their deposit like normal and they can earn a good landlord reference.2.

Could that bite our REP in year 5 when a big pile of ordinary earnings income is realized (if they don’t 1031 and defer it)?

This is more tax efficient as the interest you collect would be subject to ordinary income (outside of an IRA, whereas in an IRA, there’d be no tax on this.

Last year we created a masterclass for helping ordinary people become the Local Developer in their community so that you can be empowered to do your own deals.

Most everyone that you've described or hope to reach is either an investor, an already learned and savvy buyer/seller, or a cheapskate, and that just doesn't fit the prototype of what the vast number of buyers and sellers are - ordinary people who just want a fair price on a house and to get in and out safely without having to learn the RE industry themselves or spend a lot of effort on the process.

@Rud Sev Your Section 1231 losses from the sale of rental properties were likely correctly reported on Form 4797 (Part I) as ordinary losses, allowing them to offset all types of income.

I think when evaluating anything we should be critical of what is ordinary and what is extraordinary.

Last year we created a masterclass for helping ordinary people become the Local Developer in their community so that you can be empowered to do your own deals.

If you operate the vacation rental as a short term rental, you will be able to take advantage of taking any losses you have on the property against your ordinary income.