I know taking the first step can be the scariest, but if you keep at it, overcome obstacles, and keep your eye on the math, you'll do great!

As a landlord of a detached property, at least you can look at the roof or air conditioner to see if you might have a surprise bill in the pipeline. 

I have a large 2 car detached right now and still use my spare van as a shed. 

I lucked out last year by finding a single family detached property in Bed-Stuy with a R6A zoning where they're building 6 condos now, which I assigned for a 6 figure paycheck so I have to learn more about what can be built in a given zoning. 

For single family residence I could easily run comps by looking at Zillow and getting a handle on an area, through recent sales and valuations.This becomes much harder when analyzing multifamily since there are fewer comps, and there are other factors to figure out, such as what are the units in one apartment building renting for.This is my biggest obstacle at the moment.

The big obstacle with using the VA is that I have to live in the property for 2 years until I can rent it out.

Also on the property is a  30' x 70' detached garage. 

I am looking for a Real Estate Broker who specializes in investment properties single family attach/detached and multifamily.

The highest rents for beach houses tend to be on Sulllivans but they're the most expensive to buy as well with most detached houses out there being over a mil.  

(I know it's a silly question but it's an obstacle in having)