No one here is going to be able to give you a straight answer.In terms of finding good materials at good prices, there are generally areas off the beaten path where contractors go, but it might require a wholesale license.

I would look into a DSCR loan option it will require 15-25% down depending on the lender but it's based off the asset and if it debt services rather than based off the individual. 

After the 2008-2010 recession, FHA made changes to their MI requirements that made MI permanent on their 30 year fixed rate loans.  

DIY has its advantages.Does Whitesboro not require permitting yet?

Note that if your property is in a flood plain, banks will require flood insurance during the entire term of any loan on the property, which can be pricey.

STL CTY has a occupancy inspection requirement.

…on the other hand, flipping, BRRR'ing, wholesaling, and out-of-state investing are more like double black diamonds—they require a lot of experience, and a single mistake could have dire consequences.The fact of the matter is: real estate is a high-stakes endeavor, and the more advanced strategies (like BRRR'ing, wholesaling, flipping, out of state investing, etc.) can easily bankrupt a beginner when they're executed poorly.Although HH’ing is a strategy that's good for beginners, it’s not just for beginners—there are plenty of very experienced RE investors worth many millions who continue to HH, because it's such a powerful strategy.Now, having said all that, house hacking is not necessarily easy, and it’s definitely not risk-free (if it were, everyone would do it!)...

Yes, you will be required to pay income taxes on your withdrawal based on your year-end income vs expenses.  

Just FYI - If you have a substantial renovation to a 3 family, you will be required to add a fire sprinkler system in Massachusetts.

Depending on your personal finances, shopping for a triplex or quadplex may require the existing market rents to pass a self sufficiency test, to ensure that you will be able to pay the note.