Section 8 rentals are frequently located in extremely low barrier of entry markets, especially the single-family homes and small multi-family properties which I assume has also led to an influx of inventory.

I own one multifamily property (6 units) and a few duplexes and single family homes. 

A single-family home will be more than $400/mo guaranteed. 

A lifelong friend and I are motivated to (virtually) meet and connect with those in REI working in the Pittsburgh area.I'm active duty military and living in California with two rental properties (one in Virginia Beach & one in Pittsburgh) and my close friend owns a single family in Baltimore.  

If you truly believe you have credible capabilities and commitment, you’ll need to convince them that you are worth the risk (which likely will be a hard sell).

Investment Info:Single-family residence buy & hold investment.

Does anyone know, or have a good idea, about the difference in returns on entitling & developing the land for each scenario, with final objective to sell to a builder to build and sell the structures him/herself. ...

That said it is possible that you need to evaluate your stays and decide if it is worth taking shorter stays or sticking to some longer stays to reduce your time commitment and maximize the revenue for time invested.

I'm wondering if anyone has had experience with a similar situation to mine and or has any advice.I'm looking to buy a triplex as well as a single family home that is on one parcel, so 4 total units.

I would lean towards recommending that you pursue the deal - plus having the property remain in your family may be a net positive for you and your extended family regardless of the ultimate financial return.