I've done this with my properties because I'm well known in my small town and don't want people to know what I own.LEGAL PROTECTION: By placing your assets in an LLC, you are legally separating them from your personal assets.

I used to pay a professional bookkeeper to manage the books for our small portfolio.

I have been looking at rental properties in Connecticut (where I live), but I was thinking I might be able to get more cash flow with an Airbnb.I have seen these small cabins in southern Vermont on Airbnb.

I had a foundation guy look at mine and he suggested I put a small modine heater in my enclosed crawl space to mitigate the winter frost heaves that affect my foundation.

We had a small portfolio of Hard Money Loans over the years that have since been paid off so not new to the lending side. 

Our traditional tenants handle small things like a light bulb out or running toilet but it's a something we handle for our PadSplit homes.

There is only a small fee to accept the offer and make the deposit into a checking account.

Nope.. developers by and large are not going to cash you out and take the entitlement risk for such a small discount.. maybe 500k discount they would but not 100k.. not going to happen unless you find a developer that is not very bright and has money burning a hole in their pocket.

Once you factor that in, your small loss is actually a bigger loss once you need to do any repairs or upkeep. 

You’ll also be trading off appreciation for cash flow in those areas, so make sure to keep that in mind.If you’re eyeing a B/B+ neighborhood instead—think exurbs like Adamsville or Pleasant Grove in the west and Odenville in the east—you’ll likely be limited to condos or small fixer-uppers.