The way I've valued multifamily properties is to calculate the Net Operating Income (Gross Income - Expenses) and then divide by desired cap rate.  

Room has AV equipment and internet if desired.

There is also a large Victorian Home in the historic district (in city limits) that would be a possibility because it's more space and closer to Downtown but still a desirable neighborhood.

Sure you can find rental properties under 100k still but they most certainly will not be in a desirable area.  

The neighborhood is about 10 minutes form a lesser desirable area to the east (across a freeway), and the main road is busy/larger.

Long Island will always be a desirable market. 

A brand new building with commercial space on the first floor could mean new restaurants, shops, and businesses for the neighborhood, all of which would mean the area would become a more desirable area to live, and your property price would likely benefit as a result.  

investors holding a note secured by a assisted living facility will require an interest rate of 9 - 14% depending on desirability of property and strength of operator/borrower.  

We have some properties in LLCs but it is always because our bank has required it not out of our desire.

You get the benefit of 2 years+ of appreciation, tax free gains, protect yourself from buying in a crappy neighborhood because it looks good on paper - you're going to live there...the best test for a good investment location is if it is a desirable place to live - and your risk of running out of cash is lower because you can take your time.