It really comes down to the individual property as well and how well it's been maintained/age of the current capex items.In most cases though on single family homes, for maintenance and capex I like to use at least $150 each for both of those per month.

single-family, multi-family, etc. 2) What is your intended strategy?

Since I have never made a deal before nor do I have a lot of cash to start, I don't know if I should start small with a single-family house or if I should try to pull some investors together and start straight away with some multifamily properties.

You’re moving from single-family to multifamily investing, consider DSCR or commercial loans that qualify based on rental income instead of personal income.

Then eventually jumped from my 9-5  I've bought single family, Duplex, Triplex, Fouplexes and even a 10-Unit. 

Single family homes and multi-families. 

I currently have a single family rental in Boiling Springs, SC.

Single family and multi-families.

As an owner of a 72 unit complex and a bunch of single families I would say talk with someone in the space before you dive in too deep it is not all roses like some folks like to say, there are challenges that each type of investment poses.I saw you added a unit on another you have, be sure anything you do or buy has it permitted that way,  not fund to be on the other end of an insurance claim for something that went wrong in an unpermitted unit. 

On top of this I am over 10 years in as a landlord without a single missed payment of rent and 0 evictions.There are many more perks of staying local from lending, property management,  and most importantly fast tracking yourself to property number 2.