We have roughly $2 Million in equity today and generate enough cash flow each year to support our chosen lifestyle (which is admittedly pretty low key). 

On our own projects, we always make our own assessments of rental rates, and there are numerous resources for this data once you know where to look.You need to determine the business plan, i.e. duplexes vs. larger project, then have an architect layout the design on your chosen path, then run a set of number (proforma) to determine feasibility.

You see, I want to make my first purchase within the next 12 months, but I haven't actually chosen a region just yet. 

If turns out to be a rental (which is my expectation) then I will bank the cashflow and work towards the BRRRR strategy to add another property in the near future.What I’ve been doing lately to make dreams realty:-Listened to one or two BP Podcasts a day-Spent tons of spare time on Zillow browsing properties-Identified a single family property that has real potential to be my first deal-Gotten an insurance quote and dug up tax records on the property-Talked to a couple area realtors and chosen one whose background and experience best fits my goals-Toured the property-Crunched tons of numbers based on different scenarios-Arranged a second showing for tomorrow, with a local contractor who will be joining me for the showing to provide a quote on the work that would be needed.I am super excited for tomorrow!

If the Master policy is insured correctly then this should satisfy your lender, however, if the association has chosen to cut corners and is not fullying ensuring the property/building then your lender might require you to purchase flood insurance to balance the requirements of the loan.

So once we let a tenant know they’ve been chosen we give them 48 hours to put down the deposit which holds the unit until they sign the lease.

The fourplex is 1,015 for 1st and 2nd floor and there’s land all in front big enough for a parking garage or another fourplex if chosen to do so... the MLS is even throwing me off.

Liquor and porn always was chosen first.

Also, if my goal is to purchase a multifamily home - live in one side and rent the other side - do they (and if they do, how will they) include the potential rental income into the mortgage if I don't have a property yet chosen?

The numbers in the tool are as reliable as the data chosen to perform the analysis, and that is up to you, not the software.The tool currently uses Zillow data to suggest a number of comps for you, however you still have do the work of verifying their suitability for your analysis.