The cash flow is good when you actually get the rent and make the expensive repairs to these old buildings but the lack of appreciation really sucks so I’m back to investing in St.

They do require that a permit be acquired (super easy) and hotel tax get paid (a little more complex but there are ways to make it easy), but otherwise there are no regulations to speak of.  

People who live in expensive areas often buy rentals in less expensive areas simply because the numbers don't work where they live. 

the reality is long term rent ready MLS purchases in So Cal purchased at high LTV bleed cash when using realistic expense estimates have huge negative cash flow.  

What did you end up deciding Eric.. same boat here.. last year I put it on Sch C and paid Unemployment tax but not sure that was the right answer.. 

I think people are leaning toward fire only - no windstorm right now if you can since it is getting crazizy expensive.

From there, I'd like to expand in the STR market but as I learn, I'm open to other options.I love the Boston area but it's so expensive here and I don't know how to make that profitable.

It definitely is not the quickest route but over time you could be looking at a lot of paid off well cash flowing properties.

Is it to find and support your deal inputs (i.e. market data, lending terms, operating expense budget, etc.)?

Also if you have a business for just buying/selling land only and spend money/milage traveling to properties BUT don't make any revenue from the business the first year can you write off those expenses?