I’ve worked with investors looking to hold land for similar goals; either to build their dream home or simply take advantage of appreciation.

You should be able to get some people there who are qualified to do that kind of research for you. 

When people bring up Subject To (very risky) and private money it's usually because they have seen a lot of scaling content.

Some people have gotten lucky in the past, and the market has carried them through everything.

Add new people to your list every year, rinse and repeat.

However, if you spend time on other investing forums (outside of real estate) you will see there are lots of ways people are capitalizing during this time.

Most people didn't want to touch it.

I would apply to all of my dream homes and trust that the landlords can't refuse me because I would be protected under the Fair Housing Act. 

I don’t know how 2 people got 3 homestead exemptions but that seems like something the local taxing authority could catch pretty easy.

No off-street parking = not worth doing MTR unless it meets all of the following: super urban area where no parking is the norm, highly desirable area with a ton of MTR demand, super safe part of the city, and has great public transportation (think NYC, Hoboken NJ, etc.)Unless it meets all of the criteria above, I pass on those opportunities because my MTR will be eliminating the many people that travel with their vehicles.