A private lender is optimal (so you don't have to use all of your cash and can scale easier if desired) because you may not have to jump through as many hoops.

It could be a good option if the investor strongly desires ease and passive style.

I also never had to worry about vacancies: if you own a desirable property, you will always have people lined up to rent from you.

Maybe we could combine our desire for a meetup in the Huntington area work on getting people to attend together.

Expensive markets are often desirable because many people want to live there, driving up demand and prices.Reno, NV, for instance, is a market that benefits from diversified employment sectors, including tech manufacturing, hospitality, and recreation.

The neighborhoods are not upscale but they are desirable so good tenants are typically found quickly. 

My interest in real estate came from a desire to have stability and time/financial freedom.

@Reeti PeshawariaIf it's a desirable place to be you can STR within structure of the current rules.

It is in an extremely desirable area in Watertown, CT. 

Most often it's in free & clear properties but, in a high enough desire area like these, and with low enough mortgage balance, yup, some can 100% get enough on the sale to have it all make sense because as @Jay Hinrichs has pointed out that in these areas the majority value is in the land not the structures on the land.