Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

Go with what you feel comfortable with.4.

Is it as simple as getting the site designed and engineered for the footprint, cleared and graded (all of which I am comfortable with), and then hiring a GC to build the building?

At the time, his offer was low, and I had potential plans for that space, so I turned him down.

Off market deals usually have nonrefundable deposits and a clunkier process that isn't as suited for out of state people until they have good contacts in the area to evaluate the property (mostly contractors that feel comfortable evaluating projects for you).

I had just mastered the original deal analysis and was getting comfortable analyzing deals.  

I felt I had a good head start since I was already a real estate agent and was very comfortable with finding comps and figuring out the ARV.

I’d recommend waiting till you have a cushion of some sort depending on your comfort level before you take the plunge and buy the second deal.

The sale of our home will provide us with approximately $150,000 to allocate toward investments.At this stage, we feel most comfortable focusing on long-term rentals.

I'd feel comfortable investing ~$50k to start off.