They could self manage for several years, using the rental income, until the next phase of their retirement.If they have a decent amount of financial discipline, they may want to get a HELOC now before they build to get the most favorable rate.

Since we will be investing remotely, we plan to work with a property management company to oversee day-to-day operations.Does this sound like a solid strategy for a first investment property?

I think both of your strategies have merit, but here’s my take based on what you’ve laid out.Moving to a rent-stabilized apartment and renting out your condo as a mid-term rental could be a smart pivot, especially with its location near a hospital and LGA.

If there isn’t significant equity capture at this purchase price, and it’s not in a great location, this would be a pass for me.

I have some flexibility but rely heavily on my team for admin work and the day-to-day operations of property management.

Nobody watches your money like you do, you'll learn how to manage, so you can manage a manager later and you'll save precious early-years cash flow, which allows you to scale faster, especially in the first 5 years.

The key to investing out of state is finding a good property manager.  

. - Has accumulated tens or hundreds of thousands of dollars- Has a thesis to purchase extremely distressed office buildings in urban locations, get them re-occupied, self-manage and work in and on the buildings to get them re-rented, preferably Denver.

Idk if I like this tertiary of a location way outside of DFW.

I agree that the best way to make money is self manage your short term rental (not AirBNB, that is a platform).