However, I am not 100 percent sure this would be consistent income so it's kind of a gamble.

I've also been doing research on properties and came across Roofstock, which seems to be pretty convenient.

Should I wait and gamble that they won’t sell so I can do a conventional loan to buy both? 

I really prefer to be in Brooklyn for the convenience of being close, no crazy traffic congestion from Jersey residents clogging the SI expressway, and no tolls.I would like to discuss further though, how could I reach you?

I see it as more of a gamble than an investment.  

For long term, this is a perfect home and I don't mind living here for a while and it's one I can have my parents live in as well due to it's convenient location, so I don't mind having it as a buy and hold/short term rental combo but I'm scared of the foundation aspects because I don't really understand the scope of what this means. 

Should you decide to gamble on your crystal ball and you manage to achieve 100% occupancy with an average rent of $735 a unit, that puts your GRI @ $52,920.

What’s convenient for them?

There are a ton of potential military tenants and/or buyers since it's so close to base, making it a convenient commute for military personnel. 

For me it very convenient to just log in to the owner portal and have the ability review cashflow/p&l statements, download expense reports for each property, pull lease agreements, make owner contributions for repairs if necessary, etc. so when I am dealing with my banker in getting a new loan for a property, I can provide him the financial info on my rental portfolio quickly.