In my experience it is common and customary for the landlord or builder to provide TIA, tenant improvement allowance, to the tenant to assist if not cover the majority of the internal buildout. 

I find it's very personal, and dependent a lot on your goals, resources, risk tolerance, location, experience, etc.

Does anyone have any experience with using an FHA 203k Loan on a multi and turning it into a house hack in Massachusetts? 

What’s been your experience with real estate education programs?

In my experience in MO, land bank properties are very low priced (these are generally properties/parcels that weren't sold at the tax auction), but they often have significant tax liens on them that must be cleared in addition to the "sale price" AND they require a significant amount of rehab in order for the properties to be inhabitable. 

Im dedicated to learn this bisiness and gain the experience the right way.

In my experiences, it really comes down to the tenants that create either a management headache or a super easy investment.

I'm a pretty handy guy but this would be outside of my realm, but my experience helps me understand how much this type of improvement should cost.Improvements: remodel kitchen and bathroom, paint interior, fix exterior scafolding.How should I go about finding a contractor?

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

This shift will increase the pressure for transportation to and from job centers.