If you are willing to do this over a long period of time, this can be a great strategy, especially in a low-inventory market.

After talking to support (who were actually quite responsive and helpful), they told me I had to publish the ad with only one photo first and then re-post the ad with additional photos later to force the first photo to be first.

One of the major issues I see is this.

This can sometimes help with regulations and building codes.Just my 2 cents. :)

This also leads owners to ASSUME simpler is better when it comes to management contracts.

I’m in the 33% tax bracket through my real job and this could be a big difference in taxes owed if we sold the property?

Take it one step at a time—you’ve got this!

Would this be a feasible plan?

@Lee Sanders, if you are interested in Worcester, I would be glad to help. 

Found T&H realty services to be pretty interesting as they provide both buyer brokerage service (to help me find deals) as well as do property management i.e. they are not full turnkey provider necessarily, but reduces some of the hassle for me I guess as an out of state investor.