Quote from @Landon Sheveland: Curb appeal to attract attention, then kitchens and bathrooms are usually the most important areas to focus on.

Haven't been there, but pay attention to the foundation - if the floors are level there no action needed.

I’ve built relationships with brokers who specialize in Harlem, and one of them brought this off-market deal to my attention.

However, if your business owns real estate, that portion of the sale may qualify for a 1031 exchange, allowing you to defer capital gains taxes by reinvesting in another like-kind property.

I would focus my attentions here and try to stay local (within a 4 hour drive) as the POH rentals require more engagement.Financing is a tough deal... but sometimes you can find those Mom and Pop operations with quite a few POH rentals that will work with seller financing on a reasonable interest rate with a balloon within 5-7 years. 

I would sell and take your gains.

What would the capital gains be on the sale of each lot? 

Run through some of the features you will need like setting up a property, moving in a tenant, receiving rent payments, and publishing online applications.Pay attention to which platform feels the best to you as you perform these functions.

I don't have much experience dealing with Section 8 and I wonder whether there's a risk of bringing attention to a non-conforming rental to the Section 8 authorities. 

(Anything that isn’t your primwry first is only tax free on a pro-rated basis.)I don’t know how you could swing it but…If they gifted you the kand they would avoid their capital gains tax.