beginner Cash flow strategies

[Dustin Murphy]

Hello all, very interested beginner here. I’ve started self educating on real estate investing with the goal to take action later this year or beginning of 2024. Specifically looking in the state of Wisconsin (Madison and/or Green Bay markets). However my questions apply to a more over arching strategy in addition to regional nuance. 

Q. If your ultimate goal in REI is a specific cash flow per month (example $5,000, $10,000, or $20,000), then what are your thoughts on ways to get there in the shortest amount of time if you were to reverse engineer the units/rentals needed to generate that cash flow per month? (example: should you strategize acquiring 50 single family rentals at cash flow of $200 vs multi family homes vs apartment complex etc, where you could theoretically jump right into multiples higher cash flow) Are there other factors besides the relationship to size/number of units, up front cost of acquisition, and cash flow that would be a necessary factor in acquisition of any of these solutions if they "theoretically" presented the shortest path to the desired amount of cash flow per month?

(Also understanding property management either self or outsourced would need to be accounted for in addition to many other expenses)

Lastly, is there a known “generally universal” pattern to the difficulty of acquisition of any of those types of investments vs the other (other than amount of money). Example, 50 unit apartment complex might be fastest solution, but in your area there are tons of legal road blocks or competition, so for “fill in the blank reason”, it would actually be quicker to acquire 50 individual rental homes despite the slower potential total cash flow acquisition.

Hopefully that all makes sense or at least paints a relatable picture as to insight I am hoping to gain that others may be curious about as well just starting out!

-Dustin