If I were of the mindset that I buy with higher debt terms for the sake of quicker pay off and realize higher cash flow later, it would not be a business and I would likely still be working a job.Many of the posters here are already financially free, but either chose to continue to invest, continue to work, or a combination of both, but not a necessity.

I've been able to get a healthy combination of both cashflow and appreciation from all my properties after a little TLC.

Some leave because they were fined $500 after their dog crapped on the sidewalk but the homeless guy does it with no repercussions (true story). 

I want to combine my love of teaching and my love for Real Estate.

I want to combine my love of teaching and my love for Real Estate.

.- Seeking properties that can generate $2K+ a month in combined rent after factoring in property management, insurance, and property tax expenses.Seeking Advice:- Would purchasing two houses in the Midwest to achieve $2K+ cash flow per month be a sound strategy, or do you recommend alternative approaches?

Think about multi-tenant office buildings where the interior is reconfigured, combined and separated as needed every time a new tenant moves in.  

Maybe it's possible to do it with some combination of a trailer park business model crossed with a new construction suburban development model.Like, have a few "spaces" for rent nightly/weekly/monthly for tinyhouses on trailers, and a few lots for sale/rent to permanent residents.

i do think these types of questions combine 3 things: "what does the law require," "what does the lease require," and "what should I do given the particulars of my situation"and those are distinct questions. 

I'm also a skilled handyman and was considering offering my services to other investors as a separate business venture.My question is:Is combining buy-and-hold rentals with handyman services for other investors a wise approach, or will it spread myself too thin?