That should take the most time - determining a realistic ARV and market rent should be the work of just a day or two.If the numbers all work and you've satisfied yourself with the neighborhood, it's time to put one foot in front of the other by making an offer.

What if one of the lease was 50 years for $10/mo?

Although I believe I can see the path to my first rental easily, I'm having a hard time figuring out how I'd get to the next one. 

I'm trying to verify if this is correct and if so, how much more expensive (ballpark) can the one without standard exceptions be?  

In my market the jump from a 2 to 3 is a big one, 3 to 4 not so much.

Also, one of the homes can be raised from $1,850 to $2,300 when new owner takes possession. 3 Family House6750003 3 Bedroom ApartmentsApartment 12,205.00$Apartment 2 HUD2,300.00$Apartment 3 HUD1,850.00$Total Rent Expected6,355.00$76,260.00$ExpensesSchool Tax 23-243,460.68$Town and County 20242,222.30$Insurance3,035.51$Lawn & Plow2,400.00$Repairs and Maintenance Furnaces1,231.20$Total known expenses12,349.69$NOI63,910.31$Cap Rate9.47%

Real estate wealth is not political even if one party says they want this.  

You will make more money dollar for dollar (ie. buying 4 - $100k properties will net you more than one $400,000 property.).

A team - I have been bitten too many times, relying on one cleaner, so every place I hire has to be able to provide at least 2 cleaners in case there is an issue for 1 on a turnover day. 4.

That way, you could live in one, purchase with little down since you can use a primary residence loan with a low down payment, and collect rental income on the other 3 units.