I have 20 plus years experience in sales.

Any experience in the DMV market or just with scaling in general?

I wouldn't even consider this scenario if you have no business managing a flip, and you have never done renovation projects, as that is an arena where you need to have built experience and connections to just be OK.Let's consider that you decide to save just enough ($75k) and grab a $300k single-family rental with 20% cash down (plus closing costs) and you just rent it out (not owner-occupied) and you have limited reserves.  

Lacking the capital and building experience to develop it ourselves, we want to offer the backyard as a "Developer Special" on the MLS.We’d rather not risk demolishing our home at the front of the lot.

If you don't have a lot of experience cold calling or managing a team, I would recommend using one of the companies that already have a training program, they will hire and manage the VA's for you for a small per hour fee, well worth it. 

This community has been really helpful in helping me get started to see references and experience from everyone, so thank you all for sharing knowledge!

They told us it's for their banker but not sure as I havent had experience before selling, this is our first family property to sell so I just am wondering. 

All I can speak to is the past two years working with Michelle, Michael and their team and over that time I have had nothing but a great experience. 

Courses are great if you are looking for high-level "paper experience," but the best way to learn is to jump right in.

I'm currently a buy and hold investor (utilizing various househacks), but I'm hoping to get into the STR space end of this year/early next year.In terms of your financing options, here are some things that come to mind (albeit may or may not apply to your situation):- Utilize second-home loan option (10% downpayment) if the property qualifies- Utilize a small local bank to see what loan options they may offer (perhaps some may have experience lending on STR?