Short term rentals are more time consuming (can be like a part time job - but so can managing regular rentals) but tend to produce more income.The East End of Long Island is incredibly difficult without a lot of cash - high end rentals want high end amenities and upkeep of the property (I’m thinking paint refreshed more often, power washing the house & patio, etc).  

It gives you the best return so you require less properties and with all the automations available, it's not very time consuming nor difficult. 

With that being the case however, you can run a pretty quick and dirty Comparative Market Analysis (CMA) using any of the consumer friendly real estate apps like Zillow/Redfin/etc.

It was time-consuming and it was ten years ago.

Check out the forum Real Estate Strategies > Short term and Vacation RentalsWhen I managed vacation rentals, I paid for all consumables.

The Stessa newsletter also does a nice job aggregating market information in a consumable format. 

Door to door will get you familiar with the neighborhood in a different way, you will get the insider scoop on what the consumer is ultimately wanting to know.

I want to take advantage of the position I am in now, because I know it will not last forever with no bills, living with parents etc… I would get as much as you can on these boards, learn as much as you can, read books and consume the podcast.

No, there are no regulations that implement rules concerning the type of disclosures being discussed in this context; those rules are driven by consumer protections, which have no relevance in a commercial loan transaction. 

. - Demand - The five major areas to look at are House Prices, Number of Qualified Buyers, Housing Alternatives, Consumer Preference, and Consumer expectations. - Supply - Three major areas where you get supply is New Construction, REO/Distress Properties, and current home sellers.