These loans typically require a 20% to 30% down payment depending on the scenario and DO NOT allow for owner occupancy since it’s a business purpose loan, so you’d have to rent out both units.

For a complete beginner that is trying to jump into their first deal with absolutely little to no knowledge (obviously read books and countless videos, etc), when is a good time to start paying the $100 a month to utilize PropStream?

For the investors making money typically they figure out the strategy and location that works BEST for their particular situation and then go all in on that! 

Typically at least 20% for an investment property..You may be able to create 3 STR'S, bit you need to check your local ordinances first.

Cost overruns are very typical with first-time flips, and I would strongly suggest any real estate investors, especially new ones, have access to additional funds if they find themselves going over their budget. 

Section 8 will deduct utilities that the tenant pays from those figures.David KrulacBigger Pockets Podcast #82   

We are also getting a forgiving loan of 30k for the duration of 10 years from the county for 1 unit if we rent out the 1-bed basement unit to a household with income less than 100k and at the rate defined by the city )(~1183+ utilities) for a 1 bed unit.

Mario - Taking a "paper loss" because of depreciation is typical from my perspective.

You need to know what is typical for that sort of asset in your market.

@Terri B. it's typically overkill to try to protect an asset by leveraging it this way.