I have contemplated this idea myself of renting vs. buying while accumulating rental properties over the next 20 or so years. 

I have also been contemplating going the flat box route, but was fearfully of having long wait times on shipping.

Just contemplating selling one of my STRs and buying MF.

We are in Atlantic County, NJ and contemplating our next investment.

@James Carlson I am contemplating whether another investment property in CoS makes sense.

Moreover, the owner is contemplating selling it for $350k, but it seems like a tremendous investment opportunity.

From there contemplate who or what could provide a solution for your problems.

I'm kind of sensing that the "payments" you're talking about are actually payments for the sale of the property and what you're contemplating is an Owner carry or installment sale.You can sell that property on a note and you will end up paying all the tax but it will be spread out and only taxable as it comes in as payments. 

I'm contemplating making updates to the property but am uncertain about the return on investment (ROI) I would receive.

The other way that i have contemplated using Adwords is to find clients for my construction lending business.