Welcome to the site and RE Investing! Your background will make you very successful in this industry. It sound's like you not only have the personal experience but also the direct (even 'Childhood Friendships') most people don't have with your connections/family in the building industry.
I think you're very Valid in your 2-part Theory. Regarding your First part, YES definately start a seperate entity (LLC) for your rental homes. You can even form an LLC for each individual home if you like. ex: "123 Maple St., LLC" to limit your liability. Research this as I think it's one of the safest ways to hold title to properties. Your spot on about leveraging your cash with properties to own free+clear, just make sure to purchase correctly.
Have you found out what wholesale means yet? In Detroit, we go by the rule of 65% of Fair Market After Repaired Value (FMARV). You'll often see the abbreviation as you research of just ARV but beware of bloated or false comparable home-sale prices. Wholesaling is the same in Real Estate as it is building supplies- think your buddy's excess yard vs. going to Home Depot to build your houses. But with real estate you don't just settle on a purchase (Wholesale) price of 65%- you need to subtract your repair costs, holding/closing costs, and finally YOUR profit you want to make- usually $5-10k in Detroit. The term to me means simply finding (or building!!) cheap homes and selling them quickly for that profit. I think your ability to actually build homes within numbers that make sense is amazing and could allow you to form your own unique niche in your market that others don't have access/ability- if you can build cheaper than buying existing homes. To clarify, your banker friend has clients with Vacant Land, correct? In RE, 'Vacant Properties' means an actual Home that's vacant with no owner/tennant.
"Real Estate Investing" is one of the broadest investing arenas and can be overwhelming to someone whose looking down that path for the first time. Instead, picture a cartoon wall that is called 'Real Estate Investing' The wall has 3 doors marked:
Residential
Commercial
Industrial
You see the wall? Behind the Residential door is the Corridor with more doors marked as
Bird Dogging
Wholesaling-Flipping
Rehabbing
Retailing
New Contruction (Single Family Homes)
Landlording/ Rental
Land Contract Selling (WAY more Profit than Renting. Less Headache too)
I don't think your way off in the weeds at all, Mike. Actually, it sounds like you are sitting in a very unique cat-bird seat and if you leverage all of your stated available resources, I don't see why you cant create a VERY successful enterprise for yourself in the Real Estate Industry. I look forward to hearing your progress! Please stay in touch and feel free to reach out anytime!
Patrick Karbon