I think everyone's situation is different, and each person's journey in discovering the kind of investor they want to be can be discovered by trial & error, or education through partnering with someone or learning through the books, podcasts or forums available to you. 

But in west Suffolk County, you can purchase a rental property for a reasonable price, reasonable taxes (by NY standards), and you can still fetch a strong rental income because you're close to Nassau County which has high salary earners. 

@Sean Monahan You can still inspect your properties as normal - you'll just give your standard notice and communicate that to Airbnb guests.Loftium requires long-term tenants to hold renters insurance, and Airbnb provides $1M of damage protection and a separate $1M primary liability insurance for every booking.Most repairs don't get in the way of Airbnb hosting - i.e. if the stove is out, that can be communicated to guests - and as long as repairs are made on a timely basis, there's no penalty.We sign a standard 1-year lease for the first year, and can sign a longer lease after that if both sides are happy with the process.Feel free to check out my profile and the Loftium company profile on BiggerPockets for our website with more info. 

The bedroom wasn't in the basement though so maybe the standards are different for bedrooms below grade?

After reading a few real estate books and stumbling across BP I now realize this may not have been the best strategy.

Right now I am thinking about multi family homes that provide good cash flow and slowly moving up, basically using plan 1 from THe Book on Rental Property Investing, chapter 3.

Investing in Milwaukee by Dawn Anastasi (its on lulu as an e-book).

I have been following bigger pockets podcast and reading books about real estate investing lately and I want to start Investing this year.

I can recommend a few books depending on the strategy of your choice.

Amanda HanBrandon HallTax Reform Update – Brandon Hall and Amanda Han Linda Weygant GuidesUltimate Beginners Guide Forum StickiesBP Calculators or spreadsheets uploaded by membersMy Favorite Books I have to say all of the BP books…right?