I have been in the trade show and events industry for the past 8 years, thus any piece of advice to begin my journey is absolutely welcome!

There are too many moving pieces, you need to know contractors, make sure communication is efficient, make sure the materials is needed are in store, make sure no one is over charging you.. just to name a few. 

However, if you are able to get a 3 bedroom (for example) and rent the 2 rooms at $800 a piece and your mortgage is $1,600 - $1,800 per month, I think that would be pretty doable.

Unfortunately I put the pieces together after the fact.

I'm selling a piece of land I've held for the last 13 years, and putting it towards a SFH.

You are currently at least 1 year away from financing (if you had the ability to bring everyone current today) , but if you keep the SFH you will now need a mod.Also - in reading the numbers on these homes, quite honestly none of them sound like good long term investment pieces to hold on to from a rental standpoint.

In a C neighborhood it's a piece of cake.

All pieces to the puzzle must fit or its no good. 

I'm sure that I must have missed several pertinent pieces of info.

And the number of pieces of real estate don't matter as you'll see in rule 6.2.