I mean, as an investor, I can certainly see the room for improvement for running it as a "Motel" and I also see the opportunity to monetize it as an "Apartment Building.  

My current living expenses are $1000/month including parking, and this condo includes two gated parking spots, so I could monetize those as well.

This way you can have someone market the billboard for advertisements and then you can monetize the asset once it has a greater value.    

I'm fairly experienced, and it may seem odd, but I'd be more inclined to pay for mentoring now if I were getting involved in something that was new to me because I know I would monetize it.

$3500/mo gross - $691/maintenance - $800/taxes - $75/insurance thats $1934/mo net and with depreciation running around $1536/mo my taxable portion would be around $400/mo?

Hi @Robert Seltzer - You may want to consider a Monetized Installment Sale.

With a Monetized Installment Sale you can get cash at closing and still get 30 years of tax deferral.

A monetized installment sale is another tool that can defer capital gains taxes.

A monetized installment sale will work.

I figured $600/mo net of cash flow can float quite a bit of repairs and maintenance, etc... while the tenant is paying down about $500/mo of principal.