So I do currently have income from my rental properties, however it isnt enough to cover our current costs over here for the next 6 months.

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

At $400/month/cabin, our total annual assessment income is $48,000. 

I'll add on to what the other Ben said and mention that there are exceptions based on the # of days that you rent out your home to where the income/expenses are excludable (being lesser of 14 days or 10% of total usage if under 140 personal use days).

Lastly, always keep your job and build your employment foundation because that keeps you income relevant and lendable.Hey thanks for your reply!

Westchester, although one of the hottest markets, has a ton of upside with opportunities for both cash-flow and equity. 2-4 family properties in Westchester are the 2nd most affordable in the NYC Metropolitan area (next to Suffolk County) making it easier to find cashflow opportunities when compared to the boroughs and other suburbs like Nassau.A client of ours in Westchester recently purchased a < $800K 2-family with a detached 3-car garage which brings in additional rental income - from a local business owner with commercial vehicles.

I also agree that there have been so many syndicators who's deals have dried up and they have resorted to teaching/mastermind as a source of income. 

Im a huge fan of themI think both - they will bridge the gap with middle-income renters and also appeal to the higher-income bracket.

The majority have evictions on their record, don't make enough income or have a lot of debt under their name.Comparing other rentals on Zillow, my asking rent is $1100 while other properties are trying to rent at $1200.

Since comps are limited, analyze similar nearby locations to estimate demand.When pitching investors, focus on a clear business case: expected income, expenses, occupancy, and ROI.